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Dee Hilfiger
The following podcast is a Dear Media Production.
Lauren Everts
She's a lifestyle blogger extraordinaire.
Dee Hilfiger
Fantastic.
Lauren Everts
And he's a serial entrepreneur, a very smart cookie. And now, Lauren Everts and Michael Bostick are bringing you along for the ride.
Michael Bostick
Get ready for some major realness.
Lauren Everts
Welcome to the Skinny Confidential. Him and her.
Guest Host or Interviewer
Today we're sitting down with someone who I really admire, that I really enjoyed talking with, and that is Dee Hilfiger. She's a former model, a visionary designer, entrepreneur and philanthropist. She is married to the one and the only Tommy Hilfiger. And she's known for her effortlessly sophisticated style, which you guys have to watch the YouTube because she's wearing the cutest outfit from her own brand. D O by D. In this episode, you'll get an exclusive look at how she thinks about designing her iconic Hilfiger homes, her secrets to a thriving marriage, and how she collaborates with Tommy on designing the vision. And you should also know that she is a busy mom. She has seven kids. She really does it all. D Hilfiger. Welcome to the him and her show.
Lauren Everts
This is the Skinny Confidential. Him and her.
Sponsor or Ad Reader
So happy we made this happen.
Dee Hilfiger
Yes, finally.
Co-host or Interviewer
It's been three years in the making.
Dee Hilfiger
Yes, it has.
Co-host or Interviewer
First question, dive in. I think people look at your life and they think, wow, so lucky, so easy. But it wasn't always like this for you. And I think a lot of this episode is around how you got here. So maybe to start, how did you get here?
Dee Hilfiger
Well, I mean, that's a loaded question. It's been a long journey. I don't know how far back you want me to start. Do I go back to my Dallas days?
Guest Host or Interviewer
Sure.
Dee Hilfiger
You know, it's a long story. You know, I basically. My life, you know, I had a whole life before I met Tommy. Before I met Tommy, I was married to an Italian tennis player and I was living in Monte Carlo and I was married with my husband for, I think it was maybe eight years, almost nine years. And I wound up divorcing in 2003. I had two sons and I had been divorced for three years when I met Tommy. And I met Tommy in the south of France. Like I said, I was living in Monaco, and he came to centre, paid a visit, and that's where we sort of met and became, I would say we were friends at first because we were living on different continents. And so obviously, when that relationship bloomed, you know, my life changed a lot because I moved continents, I moved to where he was, and then, you know, my life changed. But before I met Tommy. I had, you know, I was a mom.
Michael Bostick
I had.
Dee Hilfiger
Prior to marrying my, my ex husband, I had modeled, I lived in Paris. And when I stopped modeling, I actually came to New York and I was working on Wall street at Prudential Beige as a commodities assistant trader. So I mean, I've kind of feel like I've had maybe 10 lives, not even nine. I've, you know, I've bounced around. I've done all kinds of things. I've traveled many different places and you know, landed here. Here I am.
Guest Host or Interviewer
What was it like to live in Monaco?
Dee Hilfiger
Well, I mean it, it was, you know, it. I think from the outside it like seems very James Bond and very glamorous and it was. But basically, you know, I would drive my kids to school, I drive them to karate. It was kind of like living, you know, any, any other place. It's very, very small. You live in, you pay a fortune to live in a very tiny apartment. And that part of it I didn't like. So eventually we moved just outside to Rockbrun so that we could have like a bigger house. And you know, with the kids we just needed more space. And it's small and you kind of know everybody, but as a base, it's great. My kids grew up speaking two languages or three languages rather. So they're fluent in French, Italian and English. So that was great. It's safe. So, you know, like any place there is good and bad.
Co-host or Interviewer
And how did you grow up? And I'm assuming you grew up out here in the States?
Dee Hilfiger
Yeah, I grew up in Rhode island in East Greenwich, Rhode Island. My parents both immigrated. My father is from Istanbul, Turkey. My mom is. She was born in Birmingham, England, but then moved to Canada. So they actually met in Canada. And you know, I grew up in a small town in Rhode island and you know, I had one sister. My dad was super strict.
Michael Bostick
Really?
Co-host or Interviewer
What's super strict?
Dee Hilfiger
Look like, could never go to boy girl parties. Couldn't do basically anything that all my friends were doing.
Co-host or Interviewer
Taking inspiration from your dad.
Dee Hilfiger
But I wouldn't because that made me, you know, very restless. And that's part of the reason why.
Co-host or Interviewer
Tennis pro in Monaco.
Guest Host or Interviewer
Okay.
Dee Hilfiger
I wound up going to Dallas where, you know, boy girl. I went to an all girl Quaker school in high school. School, yes. So I had a very strict, you know, imagine like Turkish, English, Quaker. You know, when I got out of that and I couldn't sort of wait to get out of Rhode Island, I was looking for like, where's the farthest place I can go when I When I finally got to Dallas, it was, like, very liberating, and I had a lot of fun.
Michael Bostick
Good for you. You have impeccable taste. Have you always had such a point of view since you were younger?
Dee Hilfiger
Well, thank you for saying that, by the way. I don't know. I have my taste. I don't know if it's impeccable, but I've always, you know, since I was really young, I always was, like, focused on. Okay, my. My sister and I each had our own room, and I would pull, you know, magazine tear sheets of, like, I want my room to look like this. And so I've always, you know, from a very young age, been very sort of hyper focused on aesthetic, whether it's clothing or the way my room looks. I don't know why, but I've just always. I was born that way.
Michael Bostick
So how does Tommy approach you when you guys start dating? You said that you guys became friends first. What was. Is. Does he have, like, a hip pickup line? Does he hit on you a certain way?
Dee Hilfiger
Well, it's interesting. His. I don't know that he had. His pickup line was probably. He said to me, you know, I should be with a girl like you. So I didn't really know how to take that. I was like, oh, okay. You know, Tommy, at that time was running around. He was pretty wild in his day, I would say. And so I didn't really take that too seriously. Like I said, we were living on two different continents. And, you know, he would sort of invite me to things and then disinvite me to things. He was very scattered. He was all over the place. So I kept it, like, in the friend zone for a while until I really kind of knew and thought, like, okay, he's really serious. Because I can't, you know, move. I've got two kids. I'm not gonna move continents. You know, for just, you know, dating somebody or somebody that wants to, you know, somebody that wasn't serious. I wasn't gonna uproot my whole life.
Michael Bostick
When you guys did decide to get together, were you both aligned with designing things together, or was that something that happened slowly over time?
Dee Hilfiger
That's funny, because I remember the very first time Tommy showed me his house. I remember think, like, just sighing, like, having a big sigh of relief. Cause I was like, oh, my God. I like his house.
Michael Bostick
That's a big one.
Dee Hilfiger
I like his taste. I mean, I don't know if you've ever, like, you know, dated somebody and, like, you just can't go there because, you know, they have, like, a horrendous pillow on their couch.
Michael Bostick
Michael had black sheets when I first started dating him.
Co-host or Interviewer
Well, actually, it's the wrong choice for many reasons.
Michael Bostick
I was like, no, you fixed that. Yeah, immediately. So I understand that. So you didn't have to, like, get aligned with him on taste. You guys both had excellent taste. And when you met each other, you just expanded on that.
Dee Hilfiger
It's funny, we used to play this game when we were dating, and he used to open up a magazine, and there used to be, like, you know, a page where they show a few different items. Like, say they'll show five different bags, and he'll say, well, what's your favorite? And then I'd have to look and I'd pick. And he'd say, yeah, that's my favorite, too. So it was like. It was kind of funny, this game. We usually picked the same thing. So I was like, oh, that's interesting. Our tastes are pretty aligned.
Michael Bostick
What was the first home that you guys decided to do together, and how did that go? Because Michael and I need. Need some advice on this area.
Dee Hilfiger
So the first project we worked on together was we bought an apartment at the Plaza Hotel, which I was like, wow, that's. I mean, I can't remember what year it must have been. 2008, maybe. At that time, it had only been a hotel. So it was really exciting. And we, like.
Co-host or Interviewer
They just opened up the part of it for.
Dee Hilfiger
Yeah, okay. Exactly. And so that was the first thing we did together. And we kind of sat down and, like, thought, okay, what do we want to do?
Michael Bostick
And.
Dee Hilfiger
And we sort of wanted to make it feel like it was, like, from the old. The Plaza Hotel. So we had, like, you know, these great. Truman Capote obviously did his famous White Ball at the Plaza. So we had, like, this great Warhol of Truman Capote. And we got black and white pictures of, you know, the White ball. We wanted to make it feel sort of classic and reminiscent of that time, you know. Cause when I walked into the space, I was like, wow, if these walls could talk. Cause everybody from, you know, Maryland and the Beatles, it was. That was a very exciting project to do together. And so we kept it sort of classic. And we did, like, you know, reds and blacks. And. I don't know. I think for us, we always start with where the house is and what is the architectural style? I don't know. Where is this house that you guys are doing?
Co-host or Interviewer
No, we're redoing a house in Aust right now, so. But you don't want to like, end up with antlers on the wall. You know what I mean? Like.
Michael Bostick
Right. You don't like your cowboy hats hung. You want. Not that there's anything wrong with it, with. You can infuse it so it feels like you're in Austin without it being on the nose.
Dee Hilfiger
Yeah, yeah, yeah. I think peppered in, like, you want to have some kind of vibe where you are. I think give it something like that. But, you know, it's always about the edit and the mix and how do.
Michael Bostick
You guys work when you work on a project, because you guys have worked on so many projects, which you. Everyone needs to check out your book. Hilfiger Homes. But how do you guys conceptualize each house? Like, what's.
Guest Host or Interviewer
What's the process?
Michael Bostick
You mentioned that you first start with, like, sort of, like. I wouldn't call it a theme. What did you call it? You said a.
Dee Hilfiger
Well, we kind of do mood boards.
Michael Bostick
Mood board.
Dee Hilfiger
We'll do, like, a little bit of a mood board where, you know, we look for inspiration. So we. We look through other magazines and things, and we take.
Guest Host or Interviewer
It's.
Dee Hilfiger
You know, the design process is very similar when you're designing clothes or anything else, it's like you'll look at something else for inspiration. You might see something and say, well, I like that from the. You know, that. From that picture, but not in that color. And, you know, it's always about where you're getting your inspiration. And, you know, you can get inspiration from many different places. So we just. We travel a lot. We get to see a lot of things.
Michael Bostick
So do you pick the pieces out from everywhere and put it together? Like, how does it all come along?
Dee Hilfiger
Yeah, I mean, we. We pick what we like. You know, it's like an editing process. Yeah, it's. It. It's interesting that you ask that, because I don't feel like it's that different than designing a bag line or a clothing line or anything else. It's always about, like, a curation and an edit.
Michael Bostick
What are some challenges that you've experienced along the way of your journey?
Dee Hilfiger
Well, probably personal challenges. I mean, if I have to be honest, I think that, you know, my divorce was a huge thing in my life. It was a huge personal challenge that in one way, I feel like it kind of set me back, at least mentally, like it did. But I had to totally sort of reprogram everything after that. That was probably like, there's sort of like, my life before the divorce, my life after the divorce.
Co-host or Interviewer
Just the way you thought about relationships or life.
Dee Hilfiger
Yes. About everything. And it was like, I was probably. I'm trying to think how old I was. I was like, maybe 38, 37, 38. Around that age when I divorced. So. And I had two kids. And so that was, like, probably the biggest challenge in my life and the biggest traumatic thing that, you know, I had to start all over and figure out, you know, what to do with these kids and how not to traumatize them. What was I going to do? I'd stopped working. I mean, there was a lot. There was a lot going on for me at that time. It was a very difficult time. And then, you know, I didn't really know was I going to stay in Monaco? I didn't know I hadn't met Tommy. Then I met Tommy three years later. But it was just like, how do I build, first of all, myself back up and then, you know, how do I take care of my kids and just how do I move forward from that? Because I'd only known being married, you know, to that man. And it was a very difficult time.
Co-host or Interviewer
In hindsight, outside of, like, in the marriage. And you would obviously have not have changed the marriage. You've got two beautiful kids out of it. But are there things you would have done differently as a young person getting married, or things that you would have set up differently looking back? Because when I'm hearing you talk, it's like, you know, your life was then in Monaco, away from your family, and then it sounds like you stopped working. So I just was wondering, like, what the. What the advice your younger self would be.
Dee Hilfiger
You know, that's a typical question for me to grapple with, because I think, you know, I always sort of look at things that. That was my journey, and maybe that was all meant to happen to get to where I am. So if I change that, I might not be here today. So I kind of view it like that. But I think, you know, I married young, and I think that. I think when I did marry, I didn't take a lot of things into consideration that maybe I should have. Like, just, you know, I married somebody from a different culture. Maybe I was too young to get married. Maybe I wasn't ready to really get married. I don't know. I mean, I question those things. You can always play the. What is it? The Monday morning quarterback. I don't know. I do try to learn from those things. I think, you know, obviously, that wasn't the right decision for me. But then if I say that, then.
Co-host or Interviewer
No, no, I. I really relate to that perspective, and sometimes I Have a hard time looking back. And my dad always says, you can't drive a car looking in the rear view. But I think there's some people, like, they have the perspective of, I did that, and that's what got me to where I'm here. And then there's the others where sometimes like, hey, I shouldn't have done those things. And it's hard if you have, I think, your perspective, or maybe even mine, to kind of like go back because your life would not unfolded the way it is now.
Dee Hilfiger
Yeah. And I mean, honestly, when you think about it, okay, that marriage was a failure, but in my life, my failures have. You know, you only gain success from failure. Right. I mean, you have several failures and, you know, it's a failure in sense of the marriage, but it's not a failure in the sense of I have two amazing children from it. And, you know, it's all under the water, under the bridge. I was young, he was younger. It's passed. We're friends, we all have moved on.
Michael Bostick
That's cool that you guys are friends.
Dee Hilfiger
Yeah.
Michael Bostick
I mean, now that you. You've had the successful marriage with Tommy, what do you think the secret or the tricks are to marriage or what is maybe your. Your personal secret?
Dee Hilfiger
I think. Well, first of all, love, laughter is definitely one, I think, like, probably love, laughter and respect. Those three things go a long way when it comes to marriage, I think.
Michael Bostick
And you guys also work together like Michael and I do, which I always say it's the most challenging but rewarding thing. Like, it's so rewarding to work together, and it's so amazing to be able to work next to your spouse. But it is not without challenge. So how do you guys sort of balance that?
Dee Hilfiger
We work together in certain ways, but then we work together separately too. It's not like we're not together like working 24 7, which is nice. Which is nice. And he'll. What's interesting is he always asks me his opinion on things with Tommy Hilfiger, and I'll always ask him his opinion on things that I'm working on because I have. I'm creative director for Judith Leiber. I. I do a lot of other things. So we're both really, really busy. I think we both love working, and so we both, you know, enjoy that. So it's not like I'm sitting there like, why are you working so hard? And he's saying, well, why are you going off there? That's helpful. I mean, we work together, but then we don't work together.
Michael Bostick
I get it. I get, I totally get what you're saying. You have your own projects going on. How do you set up your day for success? What are your routines that you do? You knew I'm gonna ask you that. I knew that you were gonna ask me that question.
Dee Hilfiger
I was warned or told that I was gonna get this question. And I was thinking about it and I was like, you know, obviously we travel around a lot, so the routine thing, I love routines. I mean, I would have to say my real routine is when I wake up, I need a coffee, like first thing. I mean. Yes.
Sponsor or Ad Reader
What's your coffee order?
Dee Hilfiger
The coffee is. I have this fantastic machine. It's a Jurassic Jura. Jura J U R. Somebody bought it for me for a Christmas present. And I, I was like, what is this machine? And it's a fabulous machine. And I put in the lavazza crema coffee beans and it, you know, mixes it up and it's a machine that you push. It can make anything, any kind of coffee. So I like my espresso long. I have a couple of those and some water. And that's like how I get my day going. And then, you know, Tommy and I, when we're home, we always drive together our son to school. So we both get in the car every morning and we drive Sebastian to school and you know, and then we come back and we both, we both like to work out. Try to get like a 45 minute workout in there with a trainer.
Michael Bostick
What's your workout? Are you guys lifting? Pilates.
Dee Hilfiger
So we're doing. Yeah, we're lifting. We're doing more strength training. And I sometimes go to a Pilates with a couple of girlfriends in Palm. Palm Beach. And, you know, we are doing the best we can with that to try to keep it, you know, keep it all, Keep it all, keeping it up.
Guest Host or Interviewer
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Sponsor or Ad Reader
Listen up everybody.
Co-host or Interviewer
Big news.
Sponsor or Ad Reader
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Guest Host or Interviewer
Of my main concerns when it comes to my skin care is my under eyes. I take it very, very seriously. And what I notice is whenever I have to wake up really early with my kids, I'll have like puffy eye bags. And obviously you guys know I use an ice roller under my eyes. But I also like a really nice eye cream. And the one that I've been using lately is by Clarins. It's called total eye lift. And so how I like to use it is I like to put a little bit on index finger and then I like to pat it underneath my under eyes and I go outward. So I can also like pump the lymph a little bit and I'll open up behind my ears and let the lymphatic drainage go to work. With Clarence Total eye lift cream. Okay, so this is what it looks like. It has a retinol like technology which is really, really cool. And everything about it is designed to help the eyes. It's like a four in one eye cream, if you will. So crow's feet, even like Elevens between your eyes, which I sometimes get to even the elevens between the eyes, which happen as you age and of course, dark circles. And for me, puffiness. I absolutely love pairing my facial manipulation with their total eye lift. I think a mix of the two is so incredible to really depuff the under eyes. I've even gotten my husband into this because he sort of gets like a purple under eye situation. So if you're looking for a purple, plumper, smoother under eyes, I think this is a really great one to try. Like I said, just apply it gently underneath your eye, sort of going up. Sometimes I'll even apply it on the top of my eye. I really love this specific one by Clarins because 94 of the ingredients are of its natural origin, which I think is really, really cool. It's plant based. It also boosts collagen, which we love. Everyone loves boosting collagen after 30. I think that's an amazing benefit which really firms the skin. And I think a hot tip it comes to Clarins total eye lift is you want to apply the eye lift before serum. This is really important. So they encourage always doing the eye cream first. So do it before your serum. I think it lays really nice under makeup, which is important to me as well. For me, at this point, it's all about prevention. I am so into preventative beauty and I also like things to be non invasive. I don't want to stick any needles underneath my eyes. So it's really nice to find an eye lift cream that works. Works. This product is known to target every single wrinkle or any eye concern around the eye. So it really sort of does everything. So I wanted to know what the order, like the exact order was. So this is the order that you want to use. Cleanser, toner, eye cream, serum thinnest to thickest, and then a moisturizer. And then I like to use sunscreen after. And then if I'm doing makeup, I'll do makeup. What I'm really into is warming up the product before I use it. So I'll warm it up between my fingers and then I'll just pat, pat, pat, pat it under my under eyes, giving a little bit of lymphatic drainage. It lifts in 30 seconds. Like you can see it right away. Clarins really does think of everything when it comes to preventative beauty. I have been a fan of this brand forever. My mom used to use it and so it's really fun to be using this eye lift cream to prevent before it even happens. Don't wait until your 30s or 40s or 50s to use an anti aging cream. This one is so important to your routine. Don't neglect your under eyes. You don't want them to be puffy. This is a great one to have in your arsenal. Also, it has Harangana extract in it which is a plant retinol. This is as effective as retinol but gentle on the skin. So if you want plumper, smoother under eyes, check out Clarins Total Eye Lift. If you're looking for something gentle on the skin, this is the new generation of the best selling Clarins eye cream, the Total Eye Lift. This is available at Ulta, Sephora and on clarins.com I get mine on clarins.com Like I said, pat, pat, pat under your eye every single morning before your serum. You will love this if you want to be preventative. This one is amazing because wrinkles are reduced in 30 days. Retinol, like technology is in this product which makes it really, really superior. And the fact to me that it boosts collagen is a no brainer. If you want to firm your skin, plump your under eyes and really kick your skincare up a notch, this is such a beautiful product to use to be preventative. I want to be very thoughtful about my under eyes. It's something that I want to really take care of. It's such a delicate, fragile place and I want something that is really amazing with results, which is why I like this product so much. You guys have all seen Clarins everywhere. It's an iconic brand that everybody loves. I remember being inspired by this brand when I saw it on my mom's vanity when I was a little girl. I feel like this is something that I'll even pass on to my daughter. I've noticed firmer skin and dark circles and puffiness reduce in like three weeks. So it works like a charm. You can go to clarins.com or Ulta or Sephora.
Michael Bostick
What about your skincare routine? I'm sure you know I'm gonna ask you this too. Do you have any specifics that you reach for for skin?
Dee Hilfiger
I am, you know, I absolutely am obsessed with the PV50, the Biologique.
Guest Host or Interviewer
I need to get back on that.
Michael Bostick
I.
Guest Host or Interviewer
That's such a good one.
Dee Hilfiger
I use it like twice a day. I'm obsessed with it.
Co-host or Interviewer
I just do what you tell me.
Michael Bostick
Don't sleep on Mike. Look at Michael's skin right now. It's so shiny. It's like.
Co-host or Interviewer
But I will do what you tell me, but I don't know.
Michael Bostick
It's looking great. I can see my reflection in it.
Co-host or Interviewer
Well, the lights are pretty good.
Michael Bostick
No, but that one is a good one. What are the other.
Guest Host or Interviewer
Go to.
Dee Hilfiger
Your skin is really good, too. You guys both have. I don't know. I should be asking you about your routine.
Michael Bostick
I have some serious skincare tips. I love good skin.
Co-host or Interviewer
Well, you know, we've had so many people come on the show. Doctors and experts and estheticians, and when they explain to me that the skin is the largest organ and that like. And you start to. I think about it now the same way I think about, you know, taking care of other areas. But before, I was. Just Looked like a dusty old saddle.
Michael Bostick
Are you ready for what I just did? Because you have to hold on tight for.
Dee Hilfiger
Okay.
Michael Bostick
Okay. I had a baby two months ago. I took my placenta and put it in a cooler. Then we took the cooler across the country, but we had a doctor to a doctor in Palm Beach. Oh, the doctor extracted exosomes out of my placenta. The audience is turning out now that are one day old. Exosomes.
Co-host or Interviewer
No, no. People do this. They get exosome therapy or stem cells. They typically do it with other people's cells or other people's exosomes.
Michael Bostick
So they take the placenta's exosomes and they put it. They package it up, and then they bring it back to you, and then they put it in a needle, and then they shoot the exosomes in your face and on your hairline.
Co-host or Interviewer
But the reason that it's. Because. So the reason this is a bit novel is most people do it that way, but because it was our shared placenta. It's her. She had the placenta, but it's our.
Dee Hilfiger
I think it was her placenta.
Michael Bostick
I hope it was anything for that.
Co-host or Interviewer
It has half of my. So it's.
Michael Bostick
Technically, I'm not gonna claim the placenta.
Co-host or Interviewer
We can both. What I'm saying is we can both use that placenta for these kind of exosome procedures instead of getting it from, like, a stranger or another.
Guest Host or Interviewer
It's different.
Dee Hilfiger
So they injected it into your face.
Michael Bostick
They injected it into your face.
Co-host or Interviewer
But she's the factory, if that makes sense of the creation of the materials that usually get.
Michael Bostick
But anyone can get their exosomes pulled. And I'm not sure how. I'd have to ask the guy, but he was saying anyone can get him pulled. And. And it's obviously, like, really good for your skin and your hair and it was kind of a different one, and I swear I noticed a difference.
Dee Hilfiger
Well, I think it's working. I think you both have. You shot these exercises in your face.
Sponsor or Ad Reader
Can you imagine?
Co-host or Interviewer
When I do, it's gonna be.
Michael Bostick
He wants to shoot them into Michael in a certain area.
Dee Hilfiger
Oh, well, is that PG or should I off screen?
Co-host or Interviewer
We did a whole episode on Lapdo.
Dee Hilfiger
Now this is really getting.
Michael Bostick
It makes it grow spicy.
Co-host or Interviewer
He doesn't say that.
Michael Bostick
He said it in the episode.
Co-host or Interviewer
Says that it essentially gives you. You, like, if you are 40, maybe now you are. The cells are like, as if they were 30. Right. So it, like, helps you.
Dee Hilfiger
Oh, my God. This podcast just took a left turn.
Michael Bostick
You never know.
Co-host or Interviewer
Wow.
Dee Hilfiger
Oh, my God.
Guest Host or Interviewer
Okay.
Co-host or Interviewer
You know, we did almost have a walk off the other day. We almost had a walk off.
Michael Bostick
We did almost have a walk off.
Dee Hilfiger
No, I'm not going to walk off. This is fascinating. I love where it's going. Let's continue. You never know.
Michael Bostick
Okay, back to entrepreneurship, because we do have a lot of questions from the audience about that. What are some pivotal moments where you felt like you were really stepping into entrepreneurship, maybe with being the creative director of Judith Lederberg, launching your own brand? Give us some. Some details there.
Dee Hilfiger
I kind of fell into it accidentally because I was advising Tommy. He was doing a preppy collection. And I, you know, I grew up in Rhode island during this whole, like, the Preppy handbook. And I said, oh, I had this bag. I was describing a bag to him that I had that you could. It had buttons and you could change the covers. I was like, you know, this was the preppiest bag, and you have to do this in adult version. And I was describing it very passionately. And he's like, well, you should do that. And so that's what got me started. And so when I started to do that, I was like, well, you know, I went and made a prototype, and I went to Mindy Grossman at HSN at the time and showed her this fabulous design. So that's really, you know, when I sort of started to get into the designing aspect of fashion. Like I said, I had been in the fashion business when I was really young. I was modeling. I was modeling in Dallas when I was, you know, going to college. And then I did it a little bit in Paris. So I was like, in that aspect in the fashion industry, but never on the. The design side.
Michael Bostick
And what about what you're doing as.
Dee Hilfiger
Creative directing for Judith Lieber?
Michael Bostick
Yes.
Dee Hilfiger
So that. That came about because, you know, we were. We bought into the company Judith Leiber was sold, and it was sold to Jamie Salter at Authentic Brands Groups. They own several brands. And so that's a friend. And so we also bought into Judith Leiber, and Jamie just said, hey, Dee, why don't, you know, you're doing bags? Why don't you take over and be creative director? And I love the idea because I had known that brand for a long time, and when we first bought it, everybody was telling me that their, like, grandmother had a collection. I kept hearing that, and I was like, okay, so we need to get the younger. You know, we have to introduce it to a younger audience and do, you know, more fun, quirkier kinds of bags with it. Because it was a lot of, like, sort of floral and almost like, deco y older lady designs. And so when I took over, that's when we started to do, like, French fries and the brick phone and things that were, you know, going viral and getting a lot of attention. So that was really exciting.
Michael Bostick
You did add a lot of fresh air into the brand. When you say those things, I'm like, oh, my God, I can remember. You remember where you see it? It's really iconic. It's very smart. You're right. It did sort of have viral moments.
Dee Hilfiger
Yeah, it was really. And that was really, you know, really a lot of fun. And, you know, I still do that, and that. That gives me a lot of joy.
Michael Bostick
How do you think about real estate and where you guys decide to have homes? Is there a certain strategy that you guys adhere to?
Dee Hilfiger
Oh, that's. That's an interesting question. I mean, I would like to pretend like there's a strategy, but there's really not. I think it's, you know, Tommy and I always say it's like, you just know it. Yeah, it's kind of like meeting a guy or something. Like, you just kind of walk in that space, or you see it and you just know. It's funny, when we bought our Connecticut house, we both walked in and the realtor was like, you know, talking this room, the square foot. Like, we were both blocked out. We both looked at each other and, like, he pulled me into the room, like, where we entered, and he said, just tell her to hurry up and finish it so we could just buy this. Like, he did not even care. And I was like, I know. I mean, we just. We walked in and we knew, and that's kind of like, it's more of a gut than it is a strategy. And I don't think that. I mean, that is our strategy. It's just a gut feeling, and it's never led us wrong. Yeah, I mean, that's really it.
Michael Bostick
You told me this off air, but I would love for you to tell the audience because I know it's in your book. What is your favorite home and why is it your favorite home out of all the homes you guys do?
Dee Hilfiger
So my favorite home in the book is probably our Greenwich, Connecticut home. That was probably the second property that Tommy and I did together. And it's really kind of where we raised our son Sebastian. And that's the home that I just said. When we walked in, it was like, hurry up and finish the tour so we can buy it. Like, it was just. She didn't even need to. We were just like, walked in. We're like, we'll take it.
Michael Bostick
What are the elements that you think make a home a home?
Dee Hilfiger
It's a combination of things, I think. You know, I think about this a lot because Tommy and I have obviously bought and sold and moved a lot. And it's hard to move. It's very disruptive and it's stressful.
Michael Bostick
Right.
Dee Hilfiger
But I think at the end of the day, what I've thought about is, it's like, first of all, it's wherever you are together. Okay? I mean, I could be in, you know, it doesn't matter if I'm in a mansion or I'm in a tent. It's like where. Where I'm with. With my husband and my son is where I'm going to feel like I'm home. And, you know, it starts from there. So I think it's just, you know, it's filling a space with the people that you love and then things that you love and momentums and memories and places that you've gone. And, you know, you walk around and you see things. It's like your stuff, you know. Have you ever seen that George Carlin? He does a sketch where he's like, you know, why is it that, you know, you walk in and you never like anyone's home? It's. Cause it's their stuff. You know, you only like your stuff, so you never feel at home. It's like you're surrounded by your things and your people and, you know, you've created your own little haven in your nest and you feel safe.
Michael Bostick
How long does it take you guys, from start to finish to do the home the way you like to do it?
Dee Hilfiger
Oh, always. I mean, it never.
Co-host or Interviewer
It never stops.
Dee Hilfiger
It never stops.
Michael Bostick
So you're constantly editing?
Dee Hilfiger
Constantly.
Co-host or Interviewer
And how do you decide outside of maybe getting an incredible offer when you're going to sell something. Like, when you're like, okay, we've had this space and time to move on to the next. And are there ones that you're like, we're never selling, or is it always keeping it moving?
Dee Hilfiger
You know, we kind of. We keep it moving. It. It's sort of like, what other opportunities? I mean, I. To be honest, I never really thought we were ever going to sell the Connecticut house, But I think Covid came, and I think Tommy wanted to change, and, you know, we like to change things up. And then that's why we kind of sold Miami, because then we were going to move to Palm. You know, we just like to switch it up.
Co-host or Interviewer
So there's no, like, okay, this is the family home that we all grew up in nostalgia. You're able to say, okay, it's time to on to the next.
Dee Hilfiger
Yeah, we don't have. I mean, we're actually in the process of selling a home that he's had for over 30 years, which is our Mustique home, which is sort of a big deal. I think it's a big deal for his kids because they've also grown up there, and I think that's why it's hard. There's so many memories that you leave behind, but, you know, ultimately, you go forward, and you're going to make new memories somewhere else.
Michael Bostick
So we saw you guys in Italy one time. You guys were. We almost went and said hi, but we didn't want to disturb you.
Co-host or Interviewer
We're at Los Coglio.
Michael Bostick
We were across the restaurant from you guys, and we were kind of talking about the podcast. We didn't want to go up to you guys, but we saw that you guys were with Kris. What's the best advice that Kris Jenner's given you in business?
Dee Hilfiger
I think she's just sort of fearless.
Michael Bostick
Yeah.
Dee Hilfiger
You know, she. You know, she'll say things to me like, you know, oh, don't be. Don't be stupid, or don't be an idiot. Like, you know, she's just kind of fearless about going forward, and she's very bold, and she does it in the nicest way with the biggest smile. But she's pretty fierce, and she's, you know, I think that they've called her like a velvet hammer. I mean, she comes off, you know, but she's a very savvy, shrewd businesswoman. So I think, you know, I've learned a lot from that. It's like, you can still be shrewd and Savvy and do it with a really big smile on your face and be nice.
Co-host or Interviewer
I had the. It was during our scheduling conflicts and I had some mics in my bag and thought it, but Lauren said it would be inappropriate if I walked up to the table and threw the mics down and said, let's just do it here.
Michael Bostick
He almost threw.
Co-host or Interviewer
We'll just do the show right here. I'm like, I'm just kidding, Just kidding. I would have never done that.
Michael Bostick
When you decided to do your own own brand, what did that look like? How did you conceptualize that?
Dee Hilfiger
You know, I think it ultimately, the concept would just be, you know, for things that, you know, it's. It's my brand with my name on it. So I like to do things that I think, you know, women will feel good in, will look good in. And it's like, comes from my taste. I edit it, I curated it, and it's just really as simple as that. It's just like, what, you know, people that would think that I have good taste would trust me in producing something that would, you know, look good on them.
Michael Bostick
And when you launch your collection, what are the favorite pieces that people are really drawn to?
Dee Hilfiger
You know, we do a lot of denim and we do a lot of, like, sort of casual wear and things like the denim. There's a pair of jeans that just kind of slip on and comfortable. I travel a lot, so I. I like really comfortable, easy to wear clothes.
Michael Bostick
Me too.
Dee Hilfiger
So, I mean, it's not fussy, it's not super.
Michael Bostick
Agreed.
Dee Hilfiger
It's just like everyday, easy to wear clothes. And they're not. They're very affordable. It's just, it's, you know, I'm not pretending to be, you know, Jean Paul Gaultier or, you know, some. It's just, they're just everyday, easy to wear, comfortable clothes.
Michael Bostick
The striped sweater that you just gave me, everyone needs to go check out, it's so beautiful. Can you tell us what's that called? What's called where they can find that sweater? I'm gonna wear it over my shoulders.
Dee Hilfiger
The whole line. I'm in head to toe. This is all do too. So the new fall line, we're on Nordstrom online and we're also at some Macy's, selected Macy's stores.
Michael Bostick
What you're wearing, you guys have to go watch YouTube. Was so cute. This is all designed by you.
Dee Hilfiger
It's cute. This is all do and even the shoe. These are old shoes. I'm not doing shoes anymore. But the shoes are. Do you know the sweater, it's just kind of sort of casual wear, but it's put together and we've done like, what's kind of fun is we've done pieces that are very interchangeable. So it's like easy to sort of mix and match. You don't need to think about, oh, what top is going to go with these pants. And you know, some women are not as at ease with putting together separates as. You know, some women can do it, some women can't.
Michael Bostick
I also think too, it's sort of like a time saver.
Dee Hilfiger
Yeah.
Michael Bostick
You know, that's the way I. It's nice to have it just ready to go to grab.
Dee Hilfiger
Yeah. It's like gran. You remember grandmas with the kids and think they, they could. It's kind of like, you know, easy to put together.
Michael Bostick
When you put together an outfit yourself, what are your styling points? Because. Cause like I said earlier, you do have a great perspective and point of view on that A.
Dee Hilfiger
It's comfort. And you know, I would say that my style is more sort of classic and I lean towards more sort of classic and feminine and sort of timeless. So you're not gonna find like super trendy or I'm not trying to be like super sexy and like showing part. You know, it's just kind of easy, classic, feminine.
Michael Bostick
You know, who has a really big point of view on style? Oh yeah, well, no, I'd love to hear.
Guest Host or Interviewer
Don't.
Co-host or Interviewer
No. But I don't think it's that great.
Michael Bostick
Of a piece of sitting all quiet.
Co-host or Interviewer
I'm not. I just think that I just.
Sponsor or Ad Reader
Well, my perspective.
Co-host or Interviewer
Is it like it, it should never look like you tried so hard.
Dee Hilfiger
Yeah.
Co-host or Interviewer
Like it should just be effortlessly classic always.
Sponsor or Ad Reader
I think.
Dee Hilfiger
Yeah, I agree with that.
Guest Host or Interviewer
The other day I got a rash on my chin and one of the things I did was I immediately ran to take my probiotics. So I upped my dose because whenever.
Michael Bostick
I have any kind of rash or.
Guest Host or Interviewer
Any kind of pimples, I feel like it's my gut telling me something. The probiotics that I take are by just thrive. I have been taking this specific brand forever. I have had the founder on the podcast three times because she's so knowledgeable about the gut and the products that she has have so much integrity behind them.
Michael Bostick
They're award winning verified products and everything.
Guest Host or Interviewer
Is designed to help with your digestive health and your full body wellness.
Michael Bostick
So that's why whenever I get any.
Guest Host or Interviewer
Kind of flare up, whether it's a pimple or like I said, a rash, I reach for my Just Thrive probiotics.
Michael Bostick
You really can't go wrong.
Guest Host or Interviewer
I will take their probiotic, I will crack it open and I will put it in my kids smoothie too. They have a Just Thrive Digestive Bitters which even supports natural GLP1 production and helps you control cravings keeping you satisfied longer.
Michael Bostick
So those are probably the two products.
Guest Host or Interviewer
That I would tell you to try from this line. Those are the ones that I like to use.
Michael Bostick
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Guest Host or Interviewer
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Co-host or Interviewer
Quick break to talk about Square.
Sponsor or Ad Reader
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Co-host or Interviewer
It is to check out. What I love about it is how flexible Square is.
Sponsor or Ad Reader
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Guest Host or Interviewer
This episode is brought to you by the Skinny Confidential. I created a candle for myself. Actually I wanted to create exactly what I wanted in a perfect candle. So as the story goes, when Zaza was born, I lit all my favorite very well known candles. You guys all know these brands. And I noticed that my brand new baby was coughing so deeply I couldn't figure out what it was. But something told me that there was something in the candle. And so I talked to a lot of holistic doctors and they said that a lot of the wicks in candles have something really toxic in them and it comes out in the air when you light the candle. So I got rid of all my candles and I started fresh with beeswax candles. And while I was buying all these beeswax candles, I realized there was a gap in the market because they weren't pretty. So I set out to create my own clean, non toxic candle for a better home. I just feel like this is a better choice because this candle has three ingredients and it's scented with eucalyptus oil, which is organic, and the wick is an all natural cotton wick. So the Skinny Confidential team and I really thought of everything for you to make a better choice for the home. I got rid of all the candles in my house and this is one of the only candles that I use. If you want to grab our non toxic candle for 20 off, just go to shopskinnyconfidential.com and you'll automatically get the discount. It's 20 off at shopskinnyconfidential.com to November 1st.
Michael Bostick
When I first got together with him, he had to help me edit my wardrobe. This is, by the way, like, I.
Co-host or Interviewer
Had to throw away the.
Michael Bostick
10 years ago. 10 years ago you had to come in and we had to do a lot of donating.
Dee Hilfiger
Oh, my God. That's like a Kanye thing.
Guest Host or Interviewer
Well, I've said that actually was.
Michael Bostick
Exactly.
Co-host or Interviewer
I've said that on the show. And I don't know if you can say that anymore.
Michael Bostick
When I was 21.
Guest Host or Interviewer
This is a long time ago.
Michael Bostick
But he definitely had to help me edit it. And you do have a very specific point of view on style.
Co-host or Interviewer
No, but it's not like a. I just, I just think that it should. I just like to go, what's the.
Dee Hilfiger
Biggest turnoff for you when you see like a girl walking? I wanna know what the. Like you see a girl wearing something like, and you're like, oh my God.
Co-host or Interviewer
I banned sweatsuits in the office. I walked in and all the girls were in sweatsuits. I said, that's not what we're doing here.
Guest Host or Interviewer
No.
Co-host or Interviewer
I don't know if that was offensive, but I was like, listen, like, I'm not coming into a space that's supposed to be presentable and have people lounging around in their own.
Michael Bostick
You don't like sweatsuits?
Co-host or Interviewer
No, I don't like sweatsuits. I don't mind a sweatshirt or a sweatpant. But then I think you have to dress it up with a. Like I say either. Like, I don't like Baggy baggy.
Michael Bostick
Yeah. He says, this is what he says. He doesn't like baggy baggy.
Co-host or Interviewer
Like, you know what I mean?
Guest Host or Interviewer
I might be in baggy baggy right.
Michael Bostick
Now, but I have to lose 30 pounds after a baby, so you're not going to get me in tight.
Co-host or Interviewer
That's different. But you know, like, when I think, I think it should just look like someone has put some effort into it. Like they care. Because I think it's a reflect, like if you, it shows that you care about not a lot of things. Right. And so the things that are turn offs to me is when it's like, oh, I just rolled out like this. I'm like, no, let's not do a rollout.
Michael Bostick
His mother is a half Japanese, so she's very specific with how she puts her looks together. So I can see why.
Co-host or Interviewer
Yeah, well, you can't. Most people don't think like, hey, that's a Japanese guy when you look. But my grandma was full Japanese and she was very, like, she was very opinionated.
Dee Hilfiger
That's fascinating.
Co-host or Interviewer
Oh, no.
Dee Hilfiger
Well, Japanese have. We were talking about this earlier with Miles that they. I love that Japanese style. I was in Tokyo. But they like baggy.
Co-host or Interviewer
Yes, they like baggy in Japan, but not like sloppy.
Dee Hilfiger
Not baggy.
Guest Host or Interviewer
Baggy.
Co-host or Interviewer
I have to be careful because, listen, I work with a lot of women, but I guess I'll just say I don't like when people look sloppy, men or women.
Michael Bostick
Does Tommy ever get in a pair of sweatpants and relax or is he always dressed up?
Co-host or Interviewer
There's no problem with getting sweatpants and relaxing.
Dee Hilfiger
Just not in, I mean, when we travel. Okay, when we travel, maybe we like to be comfortable. That would be like the time where we're in sweatpants. But I, I also prefer Tommy to be, you know, sometimes he throws on his hat. I'm like, you don't really need that baseball hat, Tommy. Come on. Like you're, you know, you're an older sophisticated, like, you know, you're a fashion designer. Let's get, let's keep it, you know, not so casual.
Michael Bostick
There's a whole nother manipulation.
Guest Host or Interviewer
You just tell him that you say hats equal hair loss.
Co-host or Interviewer
Ah, I don't think that's true.
Michael Bostick
I don't think that's true. Chatgpt.
Co-host or Interviewer
I also think that as men, I'll beat up the men for a little bit as they get older. Should lean more into like the handsome, classic look.
Dee Hilfiger
Yeah.
Co-host or Interviewer
Like when you see a guy and it's like we're holding on to also.
Dee Hilfiger
Women by the way I think, I.
Co-host or Interviewer
Didn'T want to say it, but that.
Dee Hilfiger
Adhere, I would say I can say that maybe because I'm a woman, like.
Co-host or Interviewer
There was things I could get away with when I was younger that maybe I can't get away with now. And I just, I think you just gotta recognize that a little bit.
Dee Hilfiger
Yeah, I think so.
Guest Host or Interviewer
You have to tell us about your.
Michael Bostick
Amazon prime video docu series that helps female entrepreneurs, which is amazing.
Dee Hilfiger
Oh my God, I'm so excited about this show. So it is with Serena Williams.
Michael Bostick
Cool.
Dee Hilfiger
Winnie Harlow. It's with Hannah Bromfman, Isabella Grutman, Lauren Ridinger.
Michael Bostick
Oh, my gosh.
Guest Host or Interviewer
I didn't realize this was this show.
Michael Bostick
Yeah.
Dee Hilfiger
Do you know the show?
Michael Bostick
No.
Dee Hilfiger
They came and talked about it.
Michael Bostick
Keep going, keep going. I didn't realize.
Dee Hilfiger
And my girlfriend, Talia Mottola. Talia Sodhi, who's, you know, a superstar, Latino superstar. And it's really interesting. When I first told people that I was doing the show, I think they automatically go to like a housewives kind of thing. But it's not that at all. It's really sort of like a behind the scenes look at all of our lives. We all work in some capacity. We all have different sort of storylines. Like Lauren's storyline is obviously she's running this huge company, market America, and she just has been recently widowed and her struggles with that. And, you know, my story is my story where, you know, I'm, you know, starting businesses later in life and follows that. And Isabella is just starting out her jewelry line and she's got young kids and we're, you know, all friends and we're all trying to support one another. But. And then, you know, Serena has her thing. So it just sort of follows us behind the scenes to show, you know, how we're doing things. And it's really, you know, it's, it's hopefully to inspire women, you know, who are, who are thinking about maybe starting a business or wondering, you know, how we do this or what to do. It's more trying to inspire and teach women. It's not like we're not throwing drinks at each other at like a day drinking and getting in fights.
Guest Host or Interviewer
I think that's great. It's not that kind of show.
Michael Bostick
I love, love, love the female entrepreneur aspect.
Dee Hilfiger
Yeah, it's called CEO Club.
Guest Host or Interviewer
CEO Club.
Dee Hilfiger
CEO Club.
Michael Bostick
Love it. Can you leave our audience with one piece of advice for female entrepreneurs?
Dee Hilfiger
I think stay fierce. And I think that, you know, if you, if you lead with like passion and compassion and stay true to you Know what you're trying to set out to do and that you feel is the right thing to do, then you'll ultimately be successful. And one of my favorite expressions is if. And this actually comes from Kris Jenner, too, is if somebody says no, you're asking the wrong person.
Michael Bostick
Agreed.
Co-host or Interviewer
My dad used to say, talk to the head, not to the feet.
Michael Bostick
I'm gonna apply that to you too. If you say no, I'm asking the wrong person.
Co-host or Interviewer
As it relates to our relationship, who else is there to ask?
Michael Bostick
You never know.
Guest Host or Interviewer
I'll find someone.
Co-host or Interviewer
I don't have the ability to say no in our. It's kind of like a no. And then we'll circle back. Well, you have kids.
Dee Hilfiger
You're outnumbered soon, right?
Co-host or Interviewer
We have three now.
Dee Hilfiger
Oh, you have three?
Co-host or Interviewer
Yeah.
Dee Hilfiger
Wow.
Co-host or Interviewer
They're here in the city with us. We're hanging on by a thread.
Dee Hilfiger
Oh, my gosh. Are you done? Is that.
Michael Bostick
We don't know. Oh, I don't know. I can't decide. How many.
Co-host or Interviewer
What's the right number?
Guest Host or Interviewer
Three.
Dee Hilfiger
Well, we have seven combined.
Co-host or Interviewer
I know.
Michael Bostick
Seven combined.
Dee Hilfiger
I highly do not recommend that. That's a lot. That's like, you know, seven seems a little excessive.
Guest Host or Interviewer
It's fun, though.
Dee Hilfiger
It is fun. It's like a whack a mole game. It's like, you know, you've got one thing settled, and then another pops up. It's just like, you know, things are popping so boring. No, it's never boring. So if you, like, whack a mole, then I go for it.
Co-host or Interviewer
Hey, so what is the right number then?
Dee Hilfiger
If it's not seven, I'm gonna get in trouble answering that question.
Michael Bostick
She has to say seven.
Guest Host or Interviewer
Seven's the right number.
Michael Bostick
She thinks it's seven.
Co-host or Interviewer
Is it more than three, or is it like, hey, three's good. I'm just like, wink. If you catch my drift.
Dee Hilfiger
I think three is good.
Co-host or Interviewer
Yeah. I get worried because right now, well, there's, like, more physical challenges because they're so young, and you need to help them with everything and, like, get them.
Sponsor or Ad Reader
Dressed and pick them up.
Michael Bostick
But I decided to take their shoes off in Central park the other day and run around.
Dee Hilfiger
Yeah, yeah. I will just say, because I'm a lot older than you guys, and my kids are in their 30s now, I would say that. I think when kids are young, like, you guys have them, it's one thing, and it's, like, really fun, and it's tiring, but it becomes a whole different kind of responsibility when they get a little bit older.
Co-host or Interviewer
That's what I think about.
Dee Hilfiger
You're gonna have your hands full at the same time. Quick get too over ambitious with that.
Co-host or Interviewer
It's a terrible thing to say.
Michael Bostick
No, it's honest.
Co-host or Interviewer
But everyone that's a parent that talks to us that has children that are older or have gone through adolescence or teenagers say like, well, when they become that it's going to be a lot. And so I think like, if you have. Ours are five, three newborns. So it's going to come like in a big way fast all of a sudden.
Guest Host or Interviewer
Right.
Michael Bostick
Be prepared.
Dee Hilfiger
It's just at any age, it's a huge responsibility being a parent. It changes everything. You guys know that. So I mean, I can't tell people how many kids to have because I don't know what their threshold. Yeah, you know what their patients intolerance threshold is. Mine is, you know, as I've gotten older, it's gotten much less. So, you know, but like I said, we're good 7. I won't even have pets because I'm like my responsibility. Threshold is my cup runneth over with response responsibility right now.
Co-host or Interviewer
Well, and before you leave, I need to get that all girls Quaker school recommendation because.
Dee Hilfiger
The Quaker girl.
Michael Bostick
Yes, we have a giveaway going on it. Can we give away like your favorite pieces in the collection to one audience member?
Dee Hilfiger
Absolutely, yes. I'd love to do that.
Michael Bostick
Okay. All you guys have to do to win the giveaway is one personal win. You just need to follow your line, which you can tell us what the Instagram handle is.
Dee Hilfiger
It is IO Clepo.
Michael Bostick
Okay, perfect. Follow that Instagram handle and then tell us your favorite part of this episode. On my latest post at Lauren Bostick, one of you will win Dee's favorite picks from her collection. Definitely go check out her book. It's so beautiful. Hilfiger Homes. And go watch your show on Amazon prime too.
Co-host or Interviewer
When is it out?
Dee Hilfiger
It is out. I believe the early part of 2000. Next year. Okay, 2020.
Michael Bostick
What a great group of women too, right? Yeah.
Dee Hilfiger
So lucky. Really cool. It's going to be awesome. I'm really excited about it.
Michael Bostick
Dee, thank you for making this happen. We're so grateful. Come back anytime.
Dee Hilfiger
Thank you. Well, hopefully it won't take three years to come back.
Co-host or Interviewer
No, it was worth the buildup, I think.
Dee Hilfiger
And by the way, next time you see me in Italy, come over.
Michael Bostick
Oh, we will.
Co-host or Interviewer
Oh, next time.
Michael Bostick
No, no, now we will.
Dee Hilfiger
That's my favorite restaurant. We don't want to be restaurants.
Co-host or Interviewer
You know, it would have been been highly inappropriate at that time.
Dee Hilfiger
Oh, I don't think so.
Co-host or Interviewer
We were also with some unruly characters that are in our friend.
Michael Bostick
There was a lot of rose.
Co-host or Interviewer
There was a lot going on.
Guest Host or Interviewer
But next.
Dee Hilfiger
That would have been fun. Yeah. We'll come say hi next time.
Sponsor or Ad Reader
Next time for sure.
Co-host or Interviewer
And I'll probably have the mics.
Sponsor or Ad Reader
Thank you.
Dee Hilfiger
Thanks, guys.
Released: October 30, 2025
Hosts: Lauryn Evarts Bosstick & Michael Bosstick
Guest: Dee Ocleppo Hilfiger (designer, entrepreneur, philanthropist)
In this lively and candid episode, Lauryn and Michael Bosstick sit down with Dee Ocleppo Hilfiger. Dee is known for her sophistication, entrepreneurial spirit, and as the creative powerhouse behind her lifestyle and fashion ventures, including D O by D and her role as Creative Director at Judith Leiber. The conversation dives into Dee's international life journey, blending families, her design philosophy, approaches to a lasting marriage with Tommy Hilfiger, and empowering women in business—while always keeping things tangible, relatable, and humorous.
Roots and Upbringing ([01:44]):
"My dad was super strict...could never go to boy-girl parties. Couldn't do basically anything that all my friends were doing." — Dee Hilfiger [04:44]
Early Independence and Exploration ([05:03]):
Multiple Careers Before Fashion ([02:49]):
Living Abroad ([03:22]):
Meeting & Marrying Tommy Hilfiger ([06:08]):
"I wasn’t going to uproot my whole life...for just, you know, dating somebody or somebody that wasn’t serious." — Dee Hilfiger [06:20]
Shared Aesthetic ([07:31], [08:15]):
First Home Together: The Plaza Hotel Project ([08:50]):
Design Process is Like Fashion ([11:51], [12:09]):
Divorce and Reinvention ([12:15]):
Lessons from the Past ([14:10]):
"That was my journey...if I change that, I might not be here today." — Dee Hilfiger [14:10]
Keys to Relationship Success ([16:16]):
Working with a Spouse ([16:48]):
Morning Rituals & Family Time ([17:45]):
Skincare Favorites ([29:04]):
Parenting Real Talk ([57:11]):
Venturing into Bag Design & Judith Leiber ([32:32], [33:43]):
"We started to do, like, French fries and the brick phone...going viral and getting a lot of attention." — Dee Hilfiger [34:48]
Launching D O by D: Design Ethos ([41:02]):
Homebuying Approach ([35:18]):
Home as a Feeling ([37:00]):
Business Wisdom from Kris Jenner ([39:59], [56:44]):
Tips for Women Entrepreneurs ([56:08]):
On failure and growth:
"You only gain success from failure...it’s a failure in sense of the marriage, but it’s not a failure in the sense of I have two amazing children." — Dee Hilfiger [15:32]
On personal style:
"My style is more sort of classic and I lean towards...timeless. So you’re not gonna find super trendy or super sexy—just easy, classic, feminine." — Dee Hilfiger [43:41]
On family chaos:
"It's like a whack-a-mole game...never boring." — Dee Hilfiger [57:26]
The conversation is candid, supportive, and full of practical wisdom, with humor and warmth throughout. Dee is earnest, honest about challenges, and passionate about design, family, and empowering others. Lauryn and Michael keep the mood lively and relatable, mixing personal anecdotes with tactical insights.
For those seeking inspiration on navigating blended families, entrepreneurship, creativity, building enduring relationships, or simply living beautifully and authentically, this episode delivers a rich blend of personal storytelling and actionable advice. Listeners also get a sneak peek into the glamorous, yet grounded, world of Dee Ocleppo Hilfiger, punctuated by wisdom from icons like Tommy Hilfiger and Kris Jenner.
Instagram: @IOCleppo
Products: D O by D (Nordstrom, Macy’s), Judith Leiber handbags, “Hilfiger Homes” book
Upcoming: CEO Club on Amazon Prime (early 2026)
(For further context and to enter the episode’s giveaway, see @LaurenBostick’s Instagram.)