ICYMI: The Pop Icons I Styled

Summary

Climbing in Heels with Rachel Zoe: Episode Summary - "ICYMI: The Pop Icons I Styled"

Release Date: April 25, 2025
Host: Cloud10 and iHeartPodcasts

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Introduction

In the "ICYMI: The Pop Icons I Styled" episode of Climbing in Heels with Rachel Zoe, host Rachel Zoe delves into her illustrious career as a stylist in the music industry during the late 1990s and early 2000s. Joined by her producer, Mary Elizabeth, Rachel shares behind-the-scenes anecdotes, memorable interactions with pop icons, and insights into the evolving fashion landscape of the Y2K era. This episode offers an intimate look at the challenges and triumphs Rachel faced while styling some of the most iconic figures in pop music.

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Rachel's Early Career and Transition to Freelance Styling

Rachel begins by recounting her transition from a senior fashion editor at YM Magazine to a freelance stylist. This pivotal move was fueled by the exhilarating experiences she had while styling high-profile artists, which allowed her to embrace creativity outside the confines of a magazine office.

Rachel Zoe [09:59]: "This was when I made the move to go freelance... I felt so alive, honestly."

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Styling Britney Spears: "Hit Me Baby One More Time"

One of Rachel’s first major freelance gigs was styling Britney Spears for the iconic music video "Hit Me Baby One More Time." Rachel describes the intense environment of the music industry during that time, highlighting the fast-paced nature and the high stakes involved.

Rachel Zoe [07:18]: "I flew to the World Music Awards to Monaco for 24 hours... I blacked out."

Rachel shares a vivid memory of the hectic schedule, punctuated by an unexpected blackout moment when she was left alone to prepare Britney for her performance. Despite the chaos, the experience solidified Rachel’s commitment to her craft and underscored the pressures of working with mega-stars.

Rachel Zoe [11:35]: "If you mess this up, you're not working anymore."

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Managing Multiple High-Profile Clients: The Backstreet Boys

Rachel discusses her work with the Backstreet Boys, emphasizing the complexity of styling five different members, each with their unique personalities and styles. She highlights the importance of maintaining cohesion while allowing each member to express individuality.

Rachel Zoe [17:49]: "Imagine five kids different. Not one of them would dress the same, not one behave the same."

The episode details the logistical challenges Rachel faced, from managing extensive wardrobe budgets to ensuring each member maintained their signature look across various performances and shoots.

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Enchanting Moments with Enrique Iglesias

Rachel fondly recalls her collaborations with Enrique Iglesias, particularly styling him for the beloved music video "Hero." She shares personal insights into his professional demeanor and the deep bond they formed over time.

Rachel Zoe [23:19]: "Enrique is one of the most professional people you've ever known. He just is."

A poignant moment in the episode recounts the tragic news of Aaliyah’s death while Rachel was on set, adding a layer of emotional depth to her storytelling.

Rachel Zoe [25:08]: "We got the news that she died while we were on set in the desert."

Rachel also describes the serendipitous meeting of Enrique with Anna Kournikova on set, highlighting the real-life romance that blossomed from their professional relationship.

Rachel Zoe [27:40]: "They've been together ever since that."

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Creating Iconic Looks for Jessica Simpson

A standout segment covers Rachel’s work with Jessica Simpson, particularly styling her for the promotional video of The Dukes of Hazzard. Rachel details the meticulous process behind seemingly simple outfits, underscoring the effort required to achieve the perfect look.

Rachel Zoe [28:07]: "There was literally 50 belts laid out with different buckles and different straps... it was overwhelming."

Rachel explains how she transformed standard denim shorts and crop tops into memorable, screen-ready fashion statements through extensive sourcing and custom alterations.

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Y2K Fashion Accessories and Trends

Rachel and Mary Elizabeth delve into the distinctive accessories that defined the Y2K era. Rachel highlights coats, jackets, and hats as pivotal elements, noting the prevalent use of neoprene and other tech-inspired fabrics.

Rachel Zoe [31:40]: "It was neoprene. Yes, it was a lot of neoprene."

She contrasts her style preferences with prevailing trends, explaining her resistance to oversized cargo pants and her focus on a minimalist yet chic aesthetic for male clients.

Rachel Zoe [32:56]: "I was trying to go against the crop top... I was shifting into the 90s minimalism and the chic."

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Listener Questions: Rapid Fire Y2K Edition

Rachel and Mary Elizabeth engage with listener-submitted questions, offering quick-fire responses that shed light on Rachel’s preferences and experiences during the Y2K styling boom.

1. Nicest Star Styled:
   Enrique Iglesias stands out as Rachel’s favorite, reflecting their close personal and professional relationship.

   Rachel Zoe [30:07]: "Enrique. He's an angel. We were so close."

2. Wishlist Candidate:
   Jennifer Lopez emerges as a coveted styling client Rachel would have loved to work with, highlighting the allure of her iconic "Jenny from the Block" persona.

3. Standout Accessories:
   Coats and hats take precedence, with an emphasis on the technical fabrics that were emblematic of the era.

   Rachel Zoe [31:40]: "There was a lot of neoprene."

4. Thong Popularity:
   The rise of thongs is attributed to influential celebrities like Paris Hilton and Jennifer Lopez, who popularized low-slung jeans and minimalistic styles.

5. Thin Eyebrows Trend:
   Rachel explains that the thin eyebrow trend was heavily influenced by supermodels and designers like Kate Moss and Calvin Klein, aligning with the minimalistic 90s aesthetic.

   Rachel Zoe [35:29]: "Because that started because of like Calvin Klein, John Galliano, all the 90s supers."

6. Most Stubborn Client:
   While all clients presented unique challenges, Britney Spears is noted for instances where changes to outfits were made spontaneously, such as cropping a couture top moments before a performance.

   Rachel Zoe [36:55]: "Britney was definitely the one who would sort of change whatever I was working on."

7. Go-To Look on Set:
   Rachel’s personal style during the Y2K era was characterized by black denim, leather jackets, and ankle boots, prioritizing both functionality and edge.

   Rachel Zoe [38:04]: "I'd wear dark jeans... a hundred black leather jackets, and that was like my jam."

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Conclusion and Teaser for Next Episode

As the episode wraps up, Rachel hints at a forthcoming segment titled "Meltdowns," promising listeners deeper dives into the most intense and challenging moments of her styling career. She encourages followers to stay tuned for Part Two, where more candid stories and behind-the-scenes insights await.

Rachel Zoe [39:24]: "Stay tuned for Part Two of this podcast, the Meltdown episode."

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Key Takeaways

• Adaptability and Creativity: Rachel’s ability to navigate the high-pressure environment of the Y2K music industry underscores the importance of adaptability and creative problem-solving in fashion styling.

• Building Relationships: Establishing strong professional relationships with artists like Enrique Iglesias and Britney Spears was pivotal to Rachel’s success, highlighting the significance of trust and collaboration in the creative industry.

• Attention to Detail: The meticulous attention Rachel paid to every aspect of styling, from outfit selection to on-set alterations, exemplifies the dedication required to achieve iconic looks.

• Impact of Trends: The episode illustrates how major fashion trends of the Y2K era were shaped by influential celebrities and designers, emphasizing the cyclical nature of fashion and the enduring impact of stylistic innovations.

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Notable Quotes

• On Freelancing:

  "I felt so alive, honestly." — Rachel Zoe [09:59]

• On Handling Pressure:

  "If you mess this up, you're not working anymore." — Rachel Zoe [11:35]

• On Professional Relationships:

  "Enrique is one of the most professional people you've ever known. He just is." — Rachel Zoe [23:19]

• On Y2K Trends:

  "It was neoprene... very minimal." — Rachel Zoe [31:40]

• On Stylist Challenges:

  "There was literally 50 belts laid out with different buckles and different straps... it was overwhelming." — Rachel Zoe [28:07]

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Conclusion

This episode of Climbing in Heels with Rachel Zoe offers a nostalgic and insightful exploration of Rachel’s pivotal role in shaping the visual identities of some of the biggest pop icons of the Y2K era. Through personal anecdotes and professional reflections, listeners gain a deeper appreciation for the artistry and dedication involved in fashion styling at the height of pop culture's evolution.

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For those eager to hear more, don’t miss the upcoming "Meltdowns" episode, where Rachel delves into the most intense moments of her styling career.

Transcript

[Matt]

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[Ryan]

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[Rachel Zoe]

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[Rachel Zoe]

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[Matt]

Here with Joel from How to Money. Joel, I know you like a good road trip. What's the last one that you've taken? Okay, well this was a flight, not a drive, but my wife and I just got back from the Iheart Podcast Awards in Austin, Texas. That was a lot of fun and I knew it was gonna be a hectic trip, so I booked a comfortable Airbnb for us that was very walkable to downtown. It was perfect.

[Rachel Zoe]

Yeah.

[Matt]

And nothing worse than, like, spending half your trip stuck in tr when you're trying to enjoy a new city, walking, even running around on foot like that is the way to do it, man. Agreed. Yeah. And you know what hit me while I was there, Matt? How brilliant it is to list your own place on Airbnb when you're traveling, especially now that you can team up with a co host who handles everything for you. Find a co [e-mail] host.

[Rachel Zoe]

Hi, everyone. I'm Rachel Zo, and you're listening to Climbing in Heels for your weekly dose. Glamour, inspiration, and, of course, fun. My styling career really, really caught fire in the late 90s and early 2000s, and I at the time was working in the music industry. In fact, I was eating, sleeping, and breathing in the music industry. I worked with a lot of everyone's favorites. So it's very exciting and lots to discuss. So here to help me dive into some of my more famous Y2K is my producer, Mary Elizabeth. So let's get right into it.

[Mary Elizabeth]

How exciting. As Rachel mentioned, for some reason since January, you have been getting a lot of requests for quotes or stories or trending topics about your experience in your Y2K styling era. So, as you mentioned, you started in the music industry in the days when music videos were the biggest marketing tool for a label and a song.

[Rachel Zoe]

Yes.

[Mary Elizabeth]

So the days of trl, which I was obsessed with, the butterfly hair clips, the capri pants, the layering of tank tops, the Y2K fashion is back whether we like it or not. And I think before. So I put up in your story for our listeners to answer questions or ask you questions that you will answer about Y2K specifically. And it by far, in a way, got more responses than maybe any sticker I've put on your story, like, ever. So we're going to jump into listener questions that they have about Y2K and your contributions to the era. But I thought it would be fun first to lay the scene for everybody.

[Rachel Zoe]

Also, I want to sidebar. You said late 90s or I said late 90s. I wasn't. I mean, I was like a kid then.

[Mary Elizabeth]

Oh, sure. For sure.

[Rachel Zoe]

Oh, yeah, yeah. She was too young to do anything in the 90s.

[Mary Elizabeth]

Definitely not a full adult. Definitely not. Yes. I must have been wrong on that. So I thought it would be fun to first lay the scene for listeners about the iconic Music videos that you worked on. Because all the millennials like me, who know and love you from the Rachel Zoe Project, grew up in that era of, like I said, trl and waited on bated breath for our favorite pop stars to drop their music videos. And you were a part of some truly, truly iconic ones that I don't know if everybody knows.

[Rachel Zoe]

Well, I'll be honest with you. I don't know all of them, because I will be very honest with you. My life, from the minute I went freelance, I legitimately. It's like I always say to you on the regular, like, it's a blur. Like, it's an actual blur. Because the music industry was on such fire, and the amount of money being spent on every aspect of the artist, their life and all of that was so intense. And, like, the speed at which these pop stars were working, shooting, touring, performing. And I was like, me, myself, and I. With, like, one assistant with, like, 50 racks of clothes. So I like, when you say it, I'll be like, oh, my God, of course I did that. But, like, if you asked me, I could remember probably, like, a handful of them. And, like, when I hear a song now, like, of Backstreet or Enrique or Jessica Simpson or Britney, I'll be like, oh, I did that.

[Mary Elizabeth]

You're like, oh, crap. I was on set. I was actually on set.

[Rachel Zoe]

Okay. I did that look. Right?

[Mary Elizabeth]

I love it. Okay, so let's kick it off. I mean, the Y2K queen was definitely Ms. Britney Spears.

[Rachel Zoe]

Yes.

[Mary Elizabeth]

And you did work with Britney Spears.

[Rachel Zoe]

I did.

[Mary Elizabeth]

And you did work on. Correct Me if I'm wrong, Hit me, baby, one more time.

[Rachel Zoe]

I did. So that was actually one of my very first freelance jobs, because there was a woman. There is a woman out in the world. I haven't spoken to her in forever. But Haley Hill, who was my boss at YM magazine, and Haley was the senior fashion editor, fashion director at the time. And she would get booked on these big, like, commercials and stuff, and she was booked on Britney's video and stuff through.

[Mary Elizabeth]

Okay.

[Rachel Zoe]

Her manager, Sonja Muckle. Okay. And Sonia, who I remember, like, yesterday, I think I ran into her in the last couple years. It was wild. And Haley needed help, and she had two jobs booked at the same time. It was, like, one of those things. So I was still working at the magazine, and I think it was being shot on a weekend.

[Mary Elizabeth]

Okay. And so do you remember where it was being shot?

[Rachel Zoe]

No. Like, I want to see Brooklyn.

[Mary Elizabeth]

Okay.

[Rachel Zoe]

Or Queens. Like, I can't. You know, like, at a stage or studio, I can't remember. But that's for some reason feeling familiar. And she called me because she needed help. And so I went in and started just working on it and like, pulling the clothes and doing the prep and like being on set and whatever. And I. I think at the time, like, I was so obsessed with being great at my job that I never looked at stars as stars, if that makes sense. Yeah. I don't think in the moment I knew or cared that much that it was Britney. I knew, but it was more like I was such a fashion girl.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

That to me, like, if you were like, you're going on set with Karl Lagerfeld and Kate Moss, that would have given me a cold sweat panic attack.

[Mary Elizabeth]

Sure.

[Rachel Zoe]

You know what I mean? And so I think just it.

[Mary Elizabeth]

It worked in your favor that you weren't affected star shuck or just obsessed with.

[Rachel Zoe]

Exactly.

[Mary Elizabeth]

Music at the time. It served. It served you well.

[Rachel Zoe]

Yeah. I was able to, I think, maintain professionalism without like, freaking out. Because I was so young.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

You know what I mean? I was so young, but, yeah, I felt so much older than. Than these, I mean, kids, really. Some of them were, you know, like, Kevin Richardson was not a kid.

[Mary Elizabeth]

Right. Okay, so that leads me to the next group, which is the Backstreet Boys.

[Rachel Zoe]

But the Britney I want to touch on for one sec, because after I did these few jobs working with Haley, that is when that was the impetus for me going freelance, really. Because I made so much money on those jobs that I was like, what the hell am I doing? This is creative. This is fun. Like, I'm out in the world. I'm not sitting in a fluorescent lit office. You know, I'm not locked in a fashion closet. And so this was sort of like, I just felt alive, honestly. And that is when I made the move to go freelance, like, shortly after that, because then I got promoted and then I. And then I went freelance probably later that year. Left there as senior fashion editor. But it's important because as senior fashion editor, I was styling a lot of shoots for the magazine and all the covers.

[Mary Elizabeth]

Sure.

[Rachel Zoe]

And I met a lot of publicists and a lot of pop stars and actors. Like, that's where I met Gwen Stefani.

[Mary Elizabeth]

On cover shoots.

[Rachel Zoe]

On cover shoots. Drew Barry.

[Mary Elizabeth]

So that's really how you got your foot into this, like, music world.

[Rachel Zoe]

That's how I met them. The publicist, Love that later.

[Mary Elizabeth]

Would hire you.

[Rachel Zoe]

Would hire me.

[Mary Elizabeth]

Smart.

[Rachel Zoe]

So I made a lot of connections there. And then after I was working with Britney, I worked with Britney on my own a bunch. I flew to the World Music Awards to Monaco for 24 hours. I thought I was never gonna work again because I got there, I flew with her and the bodyguards and like the team. And I just remember like I had like no notice. It was sort of like, you're leaving tomorrow and she's performing at World Music Awards in Monaco and you're going. And I was so, again, I was so young, so it was like, okay, you know, I just never unpacked a suitcase and like blah, blah, blah. And I went. And I remember getting there and I remember the managing team going, okay, everybody break. Take a nap, take a shower, whatever. And you know me, Mary. Like, I don't nap, I don't sleep. But what did I do? I fucking blacked out. I blacked out. And the next thing I remember is security banging on my door telling me we had to leave. She was going on stage, I had to get her ready. I'm by myself. I had no assistant. Like I was literally. My God, that was like one of the most panicked for you of my life.

[Mary Elizabeth]

I can't even imagine it. But for you to fall asleep that hardcore because I know you sleep like.

[Rachel Zoe]

Because the light and all nighter.

[Mary Elizabeth]

Worst sleeper maybe in the history of the world. You must have been like truly exhausted. But that is, that is really.

[Rachel Zoe]

And it was terrifying. I was like, she's going to miss her performance or go on naked because.

[Mary Elizabeth]

I fell asleep and I'll never work again.

[Rachel Zoe]

And by the way, that was truly the feeling and psychology that I had probably for the rest of my career was the, Was the, like, if you this up, you're. You're not working anymore. Yeah, that's it.

[Mary Elizabeth]

So you're working with Britney. How was Britney then? Was she. She was great because this is the sort of the beginning of her mega success.

[Rachel Zoe]

She was great and I think she was great. She was cute, she was bubbly, she was fun.

[Mary Elizabeth]

Was she collaborative with you? Did she like getting dressed or was she stubborn?

[Rachel Zoe]

Uh, it was more. What I very clearly remember was that I was trying to I think make her a little sort of create a more. What do I say? Fashion, I guess, maybe less sort of ripped everything and whatever. And I was trying to do a little more fashion, I remember a little more polish. And I remember she was performing Cher song at the World Music Awards. You know, what's it in a rhythm to the. No.

[Mary Elizabeth]

Oh la da da da da yeah. Why can't I remember the name of this song?

[Rachel Zoe]

When the beat goes on goes On. Oh, my God.

[Mary Elizabeth]

Thank you. My brain hurts from thinking about that.

[Rachel Zoe]

And she was incredible. And she had, like, long hair. And I was like, okay, I'm gonna give her this, like, very Cher, like, kind of try to do this, like, Bob Mackie, like, you know, just a very, like, whatever. And I just remember it was this long, like, I believe, if I remember correctly, from 500 years ago, Donna Karan like, did this, like, custom, like, couture at that time, because we used to do all these award show dressing looks together. Like, we would do custom things for clients. But she was doing this very special. It was like this long, beaded, like, almost like a mermaid fishtail long skirt. And basically we put this top on her. And I just remember, like, two minutes before. Two minutes before she went on stage, she went in the bathroom and cut it.

[Mary Elizabeth]

She cut the couture.

[Rachel Zoe]

She cut the couture. She cropped the top to just below her boobs. If I remember correctly. I cried.

[Mary Elizabeth]

Yikes. Yeah. I mean, as the stylist, I'm sure you cried.

[Rachel Zoe]

Well, I cried only because I was like, am I fired from Donna Karen now for life?

[Mary Elizabeth]

Have I ruined my life, my reputation?

[Rachel Zoe]

Yeah. Did she hate what I styled? But she looked incredible. She performed great. We all went to this big dinner with Prince Albert. Oh, my God. And at that. That was the beginning of my very surreal life.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Really.

[Mary Elizabeth]

And that's 20 years jumped you to Backstreet Boys, which.

[Rachel Zoe]

Yes. Same. Same management. It was with the Firm, a place called the Firm, which had Enrique, Backstreet, and Brittany. And I want to say in sync, but maybe that's wrong. Well, that may.

[Mary Elizabeth]

I mean, for millennial girls like me, you were either backstreet or in sync. And there was no.

[Rachel Zoe]

Well, it's Edward or are you Jacob?

[Mary Elizabeth]

Of course.

[Rachel Zoe]

Yeah.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And now with Summer, I turn pretty. It's. Are you Conrad or are you Jeremy?

[Mary Elizabeth]

I mean, it. It's just. It goes on forever, doesn't it? Backstreet boys equal to basically Beatle mania. Beyond, in terms of, like, beyond the logistics of them traveling, touring, being. It must have been so insane to not only have one very famous client, but five very famous.

[Rachel Zoe]

I can't really explain what was happening.

[Mary Elizabeth]

So you didn't do. Correct me if I'm wrong, you didn't do the Back Streets Back music video.

[Rachel Zoe]

Right.

[Mary Elizabeth]

The one where they're like Phantom of the Opera and it's like the dance, like the Thriller vibes, where they're.

[Rachel Zoe]

That might be right when I started.

[Mary Elizabeth]

Because you started with the Millennium Album.

[Rachel Zoe]

Was that my first or was that my last into Millennial. That I literally cannot remember.

[Mary Elizabeth]

You can't remember?

[Rachel Zoe]

I have to watch that video.

[Mary Elizabeth]

Okay. But I very clearly remember, like, Michael Jackson, Thriller inspired. They're, like, dancing. It's like, sort of a Haunted Mansion vibe.

[Rachel Zoe]

Why do I feel like, what were they wearing? I could tell by what they were wearing. Like, did they look like I styled them?

[Mary Elizabeth]

No, because it was so theatrical.

[Rachel Zoe]

Right?

[Mary Elizabeth]

So, like, AJ has, like, the Phantom of the Opera mask on at one point. Like, Brian, I think it was. Brian is like a werewolf man. Like, it was very, very theatrical.

[Rachel Zoe]

I did so many music videos with them, and we did, like, there's nothing we didn't do, so it's possible. But I remember Millennium because that's the all white. Oh, well. Yeah, I remember that. Like, it was. Because I remember walking into my hotel room, I had been prepping for so long, and what you have to remember. And I need people to try and, like, visualize what my life was with Backstreet. Imagine five kids different. Like, anyone who has five kids, you could have 10 kids, and not one of them would be alike.

[Mary Elizabeth]

Sure.

[Rachel Zoe]

Not one of them would dress the same, not one behave the same. And that's what it was like. And it was, like, five guys that I loved, honestly, deeply. I was so close with them. They were like brothers. And Kevin was like, a friend. Cause I think we were the same age.

[Mary Elizabeth]

Kevin was the slightly older one in the group.

[Rachel Zoe]

And Kevin kind of felt, like, honestly, like the dad of the group, you know? And he and I hung out. I loved his girlfriend, wife, Kristen. And, you know, I went through so much with all of them. I would say Nick was the baby and really felt like the baby, you know? And I genuinely think. I just remember white, gray, black. But, like, Millennium obviously was all white. But I remember ideating with that, and I remember saying, like, it's a new century. It's a new. Like, everything should be clean. Everything should be new. And I remember, like, creating that and seeing, like, they need to look modern, they need to look cool, they need to look clean, they need to, like, look cohesive.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And that was the biggest thing that I focused on with them was cohesion. Because I felt everyone needed to have their own style and their own take on the concept, which they did.

[Mary Elizabeth]

Sure.

[Rachel Zoe]

And that was the challenge. Right. But, like, we would have. If it was five guys, I swear to God, I had a minimum of five racks per guy.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

So I would stand there with, you know, 50 racks of clothes and just white Overwhelming.

[Mary Elizabeth]

That job.

[Rachel Zoe]

White, Dolce White, Gucci White, you name it. White, Zara White, everything White. Everything. Right. Calvin White, you know, that's insane. Yeah, it was, it was overwhelming.

[Mary Elizabeth]

That's insane.

[Rachel Zoe]

My wardrobe budgets were, and remember in those days it was not like computer based. We didn't have like the cell phone world. Like, it wasn't like that. So there was like Startac phones. So we were not, I was not doing expenses on a phone. I wasn't taking notes. Everything was paper, everything was taxis, everything was food, paper, receipts, everything, everything. So if I had like a hundred thousand dollar wardrobe budget, $200,000 wardrobe budget, I had to account for every penny of that. And the worst part as a stylist, as any stylist will tell you, is you have to lay out that money and then. And then you wait.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And you wait to get reimbursed.

[Mary Elizabeth]

Oh, that's.

[Rachel Zoe]

It's a terrible model.

[Mary Elizabeth]

That's terrible.

[Rachel Zoe]

It's a terrible business model.

[Mary Elizabeth]

Literally a stomach hole.

[Rachel Zoe]

It's a terrible business model. So every bit of my free time that I didn't have was spent taping or glue sticking. Taxi receipts, food receipts, tailoring, alteration, shipping, purchasing. You know, I had to purchase a lot of stuff. I had a lot of stuff custom made. I would be like down on 8th street getting random, like things for AJ, like feather things or like I would get like embroidered or studded. Like I would buy a leather vest and have someone in 8th street just like add studs to it or grommets on the shoes or denim, rip it up. I would tie things to like a car and drive so they would get beaten down. I would wash them. I would just try and like wear things down. T shirts, I would tea stain them. I remember the tea tie, dye, you name it.

[Mary Elizabeth]

Oh my God.

[Rachel Zoe]

Any job is too much.

[Mary Elizabeth]

Yeah.

[Ryan]

It's sandal season at Dansco. That's right. Dance Go, the iconic clog brand now offers sandals. Whether you're looking for stylish wedges, comfy flats or trendy cork sandals, Dance Go has you covered. And don't miss the all new platform Pro cloud. Visit Dansko D A-N-S-K-O.com radio to explore Dansko's full range of supportive and fashionable footwear. From Dansko's iconic heritage clogs to the latest designs. Dansko's easy to wear slip ons and adjustable styles are made to support you through even the busiest days. Plus enjoy free shipping and returns. Visit Dansko D A-N-S-K-O.com radio today Ryan.

[Matt]

Reynolds here from Mint Mobile with a message for everyone paying Big Wireless Way too much. Please, for the love of everything good in this world, stop with Mint. You can get premium wireless for just $15 a month. Of course, if you enjoy overpaying. No judgments. But that's weird. Okay, one judgment anyway. Give it a [e-mail] Switch upfront payment.

[Mary Elizabeth]

Of $45 for 3 month plan equivalent to $15 per month required intro rate first 3 months only, then full price plan options available, taxes and fees extra. See full [e-mail] this is what you.

[Rachel Zoe]

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[Radhi Devlukia]

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[Mary Elizabeth]

Okay, one of my personal favorite music videos that I'm obsessed with you working on is Mr. Enrique Iglesia's hero.

[Rachel Zoe]

Oh, my God.

[Mary Elizabeth]

That song. That video. I would wait for TRL because I thought he was so gorgeous. And I also like the drama of the song in that music video with, like, Jennifer Love Hewitt and Mickey Rourke was.

[Rachel Zoe]

You had no idea.

[Mary Elizabeth]

I was obsessed with that. That video and that song.

[Rachel Zoe]

That experience was perhaps one of the craziest experiences of my styling career, of my life.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

I will remember that video forever for many reasons. That and another Enrique video where he met Anna, where he met his wife.

[Mary Elizabeth]

That is so funny.

[Rachel Zoe]

And another Enrique video where I styled him with Whitney Houston.

[Mary Elizabeth]

Oh, my God.

[Rachel Zoe]

And that was unforgettable, honestly.

[Mary Elizabeth]

That's ironic.

[Rachel Zoe]

That's so unforgettable. And her daughter came to set.

[Mary Elizabeth]

But Hero was a stressful job.

[Rachel Zoe]

So Hero was crazy because it was this director, Joseph Kahn.

[Mary Elizabeth]

Yep. Who at the time was the.

[Rachel Zoe]

Yes. The guy I worked mainly with. Joseph Khan. I worked with Francis Lawrence a lot. He did a lot of the videos.

[Mary Elizabeth]

Who now directs, like, very Major Motion.

[Rachel Zoe]

Yeah, yeah. He. That video was in Palm Springs.

[Mary Elizabeth]

Okay.

[Rachel Zoe]

At the Merv Griffin Estate.

[Mary Elizabeth]

Okay.

[Rachel Zoe]

If I remember correctly, we stayed at, you know, one of those great hotels. I remember getting there, like, two in the morning. We had to be on set at 4:30. A prop stylist actually died on their way to set.

[Mary Elizabeth]

I remember you talking about it.

[Rachel Zoe]

It was the absolute saddest thing because she drove off the ledge. There was no railing on the location we were going to. We were shooting, if I remember correctly, like, August 27th or August 28th, something like that.

[Mary Elizabeth]

In the middle of the desert.

[Rachel Zoe]

In the middle of the desert. It was 104.

[Mary Elizabeth]

No.

[Rachel Zoe]

By 7:00am oh, my God. Aaliyah died. Aaliyah died.

[Mary Elizabeth]

Oh, you got the news that she died?

[Rachel Zoe]

We got the news that she died while we were on set in the desert.

[Mary Elizabeth]

Because she was also shooting a music video in the Caribbean, right?

[Rachel Zoe]

Yep.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Her plane crashed. And so it was all these weird, weird energy. Yeah. Mickey Rourke was there. I was in a hotel. A hotel with Mickey Rourke. And that was wild.

[Mary Elizabeth]

Wild.

[Rachel Zoe]

He. By the way, he couldn't have been sweeter to me, for the record. And Jennifer Love Hewitt, I had known because we had done a bunch of shoots together because I think she had done, like, Party of Five. I had met her through ym and then I. And then I became her stylist for a bunch of things. And so I was doing her and Enrique. And, you know, Enrique is one of the most professional people you've ever known. He just is. And he would show up. He is by far and away the most handsome and charming. Love that person. Everything you want Enrique to be, he is. And more. And me styling.

[Mary Elizabeth]

To hear that.

[Rachel Zoe]

Me styling Enrique, as much as I would try and make him a little fancier at times. Jeans.

[Mary Elizabeth]

Yep.

[Rachel Zoe]

Vintage Levi's. Like, vintage jeans, hoodies, tight shirts. I got him to go sometimes from a baseball hat to a beanie.

[Mary Elizabeth]

Yes.

[Rachel Zoe]

Which ended up being like a signature. So that was a moment. I loved him. I still love him. I'll always love him. And I styled him for the video where he met his wife, Anna Kournikova. And I styled her as well. And I remember so clearly standing behind the monitor because I was obsessive about, obviously, everything. Looks, clothes, looks, clothes, everything. But the thing with me, beyond styling, I would always. I really did everything in terms of, like, I watched the lighting, I watched the angles. I would suggest to the directors how it might work better.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

I would sit in all the time. I would try, you know, like, I was so in it.

[Mary Elizabeth]

You were very present on set, every part of it.

[Rachel Zoe]

But I remember standing behind the monitor, and I remember looking at the director and looking at Enrique's team, this guy Fernando at the time. And I was like, chemistry's pretty real in this one. This may go past this video, everyone.

[Mary Elizabeth]

Something might be going on.

[Rachel Zoe]

And it did.

[Mary Elizabeth]

And they've been married for a long time.

[Rachel Zoe]

They've been together ever since that.

[Mary Elizabeth]

I love that so much. Okay, rounding out your iconic music video moments, we have to talk about Jessica Simpson.

[Rachel Zoe]

Okay.

[Mary Elizabeth]

We have to talk about. These boots were made for walk in. I mean, you fully dressed her like Daisy Duke.

[Rachel Zoe]

Right.

[Mary Elizabeth]

She had. Because that. The song was for promotional for the movie the Dukes of Hazard.

[Rachel Zoe]

That was amazing. I just watched a clip of it.

[Mary Elizabeth]

With long, long extensions in.

[Rachel Zoe]

Yep.

[Mary Elizabeth]

Ken Pavis, the tiniest denim shorts you've ever seen in your life, ever. And, like, a midriff tank top.

[Rachel Zoe]

Yep. She look.

[Mary Elizabeth]

And a big belt. Belt. Right.

[Rachel Zoe]

That belt needs to understand, because I think it's so important if you don't know what stylists do. What I need to explain to you is that when you look at that video of Jessica Simpson and you look at. Okay, she's wearing these cowboy boots, a big belt, these tiny little denim shorts, and this crop top. Okay, great. And I think we did cool earrings, if I remember correctly. She was so good in that video, honestly.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

But what nobody knows is that to get to that look, there was literally 50 belts laid out with different buckles and different Straps. There was maybe 30 pairs of cutoff denim shorts, maybe more. To make sure they were the right fit, we would have tailors on set that would make them shorter. To make them shorter, then fray them so they look vintage. Cowboy boots. I mean, a hundred pairs.

[Mary Elizabeth]

Oh, my God.

[Rachel Zoe]

And like, the T shirts, I mean, you know, I would run up and down Melrose and La Brea and go all the thrift stores and, you know, it's not what it looks like, is all I'm saying.

[Mary Elizabeth]

Well, the simplicity of, you know, denim shorts and a tank top and whatever, I think to an outsider goes, oh, that's so easy. Anyone could do that. No, but the amount of a. Approvals it takes to get to the final outfit and, baby, getting the final outfit and then keeping it, you know, you're shooting these music videos for more than one day, most likely keeping them looking good. Having multiples to put on if she rips it or drops whatever on it or whatever. It's. It's more than just a pair of shorts and a tank top.

[Rachel Zoe]

Oh, yeah, yeah. It's. It always is.

[Mary Elizabeth]

Always.

[Rachel Zoe]

It always.

[Mary Elizabeth]

Oh, he Doki. I'm gonna go rapid fire right into our listener y2k questions.

[Rachel Zoe]

Okay.

[Mary Elizabeth]

This covers a lot of different sort of like Y2K E topics, but let's do it. Let's do a rapid fire.

[Rachel Zoe]

Okay.

[Mary Elizabeth]

Okay. Question one. Who is the nicest star from that era that you dressed?

[Rachel Zoe]

I gotta tell you, I mean, you know, the Backstreet Boys, like I said, were literally. It was like. It was like almost like I was their sister.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Slash mom, you know, that always was with them. Enrique. He's an angel. He's an angel. We were so close. Like, I love.

[Mary Elizabeth]

You're too nice to say true.

[Rachel Zoe]

I would honestly tell you because anyone. That was a nightmare. Like, I. I didn't have time for honestly.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Well, that's good to know.

[Mary Elizabeth]

That's good. Was nice.

[Rachel Zoe]

And Jessica and I were, like, related.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Literally.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Like, I was part of the Simpson family at one point.

[Mary Elizabeth]

Oh, my God, I love that. Okay, who do you wish you could have styled from that era but never got to. I think you could do, like, music or otherwise.

[Rachel Zoe]

I mean, maybe JLo.

[Mary Elizabeth]

JLo.

[Rachel Zoe]

Right.

[Mary Elizabeth]

Because that was like her.

[Rachel Zoe]

Jenny from the block.

[Mary Elizabeth]

Jenny from the block. Yeah.

[Rachel Zoe]

You know.

[Mary Elizabeth]

You know who else I feel like, and I don't even know if you have worked with her, but, like, talking about, like, more 90s, whatever, but Alicia Silverstone. I did work with Cher Horowitz.

[Rachel Zoe]

I could work with her. I styled her for different shoes.

[Mary Elizabeth]

Aerosmith's muse. Right. She was in all of those music videos.

[Rachel Zoe]

Yeah.

[Mary Elizabeth]

But I feel like she. And I feel like she could have been, like, a client of yours, like, no brainer. Just with her, like, aesthetic. Okay, what accessories from Y2K stand out to you the most? Like, when you think about just accessories and having to, like, have a thousand options of blank. What is it?

[Rachel Zoe]

God, I. I'll be honest with you. Like, I remember coats.

[Mary Elizabeth]

Coats.

[Rachel Zoe]

Like, jackets and, like. And, like, accessories. I mean, hats.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

There was a lot of hats.

[Mary Elizabeth]

I feel like, also with jackets. Y2K had an interesting fabric.

[Rachel Zoe]

Yeah. It was that techie product.

[Mary Elizabeth]

Yes.

[Rachel Zoe]

It was the. That's why I keep going.

[Mary Elizabeth]

Scuba gear.

[Rachel Zoe]

It was neoprene. Yes, it was a lot of neoprene. A lot of. But the thing with me, though, truthfully, I think I'd never succumbed to the oversized cargo pant and the, like, the sneakers with the big socks and stuff. And I think that's why in its resurgence, I'm like, no, see, I didn't.

[Mary Elizabeth]

I didn't like it then.

[Rachel Zoe]

I was trying to go against the crop top. You know what I mean? Sure. So I think for me, I was shifting into, like, the 90s, like, this sort of minimalism and the. The chic and then the sort of, like, over the top. And I, you know, I was just about pretty. Yeah. But for guys, to be honest, my vibe was, like, just look hot.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Like, and to me, hot was Brad Pitt and Thelma and Louise. Like. Yeah. To me, it was always trying to make the guys. Especially with, like, Enrique, it was that, like, no, like, look like Johnny Depp with Kate Moss. Like.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Like, beat up jeans, cool belt, beat up, like, Chelsea boots and. And, like a cool, like, leather or suede jacket with a vintage tee. Like, to me, that was cool.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And that's where I was trying to take the guys, because that's where all of, like, young Hollywood. That was the young Hollywood vibe.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And so I was merging the world. I was able to do that with Enrique.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

You know.

[Mary Elizabeth]

Okay, we got this question a couple of times.

[Rachel Zoe]

Oh, my God.

[Mary Elizabeth]

Why did thongs become popular? And Y2K.

[Rachel Zoe]

Oh, my God.

[Mary Elizabeth]

It was like a thong. It was like a thong craze. I mean, there was even the song Paris Hilton.

[Rachel Zoe]

You know, I don't think we've talked about Paris Hilton here, like, Nicole and everything, because we're talking pop music. But, I mean, I think Paris was like juicy sweats.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

Which was the biggest Y2K, fashion wise. That's the thing. Like, I, I can't. We can't forget that that was JLo, Madonna and like the whole velvet tracksuit of like my friend Pam Levy and Gila that created the juicy tracksuit. And that was like rhinestone, like bedazzled tracksuits. Bedazzled jackets, kits in.

[Mary Elizabeth]

Oh, yeah.

[Rachel Zoe]

You know, the bedazzled everything. So I think we can't like not mention that because I think it's a part of Christina Aguilera, like all of them. And Christina was opening for Backstreet Boys at the time.

[Mary Elizabeth]

Oh my gosh, that's so crazy because she obviously went on to be her own massive success story.

[Rachel Zoe]

Yep.

[Mary Elizabeth]

So, yeah, the thongs, like coming out.

[Rachel Zoe]

Of the pants and then we did the, the low slung jeans.

[Mary Elizabeth]

It's almost like the thong craze happened because the jeans were just too low. Yes, the jeans were God awfully low.

[Rachel Zoe]

And just to be clear, I want to be clear, I was not an advocate for that.

[Mary Elizabeth]

Sure, sure.

[Rachel Zoe]

You know, I mean, I think Paris, like, I have such a clear visual of when I met her with like the cropped bleached white, platinum hair in like a pink velvet sweatsuit with like so low. But she looked so hot, you know?

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And she was so sweet and friendly, honestly.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

But Kitson, I just keep thinking about Kitson.

[Mary Elizabeth]

Oh, yeah, it was the craze. Okay, next up, thin eyebrows. Just why, Just why is what this our listeners?

[Rachel Zoe]

I'm gonna tell you why. Because that started because of like Calvin Klein, John Galliano, all the 90s supers. Kate Moss, they all did it.

[Mary Elizabeth]

Which we parted their eyebrows off.

[Rachel Zoe]

It was part of the minimal, the, you know, the minimalism movement. And it was all the 90s with matte brown makeup, you know, very neutral palette. Matte, matte lips, thin, thin eyebrows, very wavy movement and very minimal. No bells and whistles, no jewels, Very clean. It was the, the Kate Moss Calvin movement. Honestly.

[Mary Elizabeth]

Yeah.

[Rachel Zoe]

And Kate Moss, like, I mean, she was like 16.

[Mary Elizabeth]

I know.

[Rachel Zoe]

I mean she, she changed the whole.

[Mary Elizabeth]

I mean, some of us millennial girls are paying for the over tweezing.

[Rachel Zoe]

I would like to proudly say that my mother. I have to thank my mom for not letting me do that.

[Mary Elizabeth]

That's good.

[Rachel Zoe]

Because I still to this day have eyebrows.

[Mary Elizabeth]

Blessed. You made it out.

[Rachel Zoe]

I still have.

[Mary Elizabeth]

You made it out of Y2K with your best.

[Rachel Zoe]

I mean, I don't. Listen, I don't have my 90s 2000 eyebrows, but I still have eyebrows. Fair.

[Mary Elizabeth]

Okie dokie. Last question. Who was Your most stubborn client from Y2K doesn't mean mean or difficult, but who was the most stubborn when it came to, like, getting dressed or wearing what you recommended or.

[Rachel Zoe]

You know, when I think about it, it's like this sort of, like, the Lindsay Misha Nicole. We had so much fun. So they. They weren't. I'm thinking about my music world. Like, I mean, Britney, I would say, definitely was the one who would sort of, like, change from whatever my.

[Mary Elizabeth]

Well, after you told me the cutting the couture story.

[Rachel Zoe]

Yeah, I mean, I think Britney was definitely probably the one that, you know, did that. And I think I'm thinking about some of the Backstreet Boys. Like, we really collaborated. I mean, AJ And I had so much fun because he was the most, like, out there, you know? Yeah, we would. He was the most costumey.

[Mary Elizabeth]

He was like. He was like the. Well, like, the bad boy of the backstory.

[Rachel Zoe]

Oh, for sure.

[Mary Elizabeth]

So he was, like, the risk taker.

[Rachel Zoe]

Yeah. And he had the most incredible voice. And Kevin was, like, dressing like my brother. It was fun. Nick. It was like, chasing him to put clothes on him.

[Mary Elizabeth]

Oh, my God. That's. I mean, because he's just, like, running around enjoying his.

[Rachel Zoe]

And Brian was, like, a gentleman, you know, and how. He was a doll.

[Mary Elizabeth]

Okay, this is your final question.

[Rachel Zoe]

Okay.

[Mary Elizabeth]

What was your go to look in the Y2K era when you were on set, when you were traveling, when you.

[Rachel Zoe]

Were black and jeans? Like, I would wear dark jeans. I'd wear, like, flare, obviously. Yeah, always dark denim. Some kind of, like, black. Probably ankle boot, you know, some kind of boot and like, a. Like a. Like a black, like, leather jacket. I had, like, a hundred black leather jackets, and that was, like, my jam.

[Mary Elizabeth]

Your go to.

[Rachel Zoe]

Yeah.

[Mary Elizabeth]

Stylists always need pockets.

[Rachel Zoe]

Pockets. It's so funny. It was so fast. I'd, like, think about what I was even wearing. I can't even, like. Yeah, I never thought about me.

[Mary Elizabeth]

Right. Well, because you said you, like. I kept a suitcase packed, so you're just, like, bringing the same things over and over, I'm sure.

[Rachel Zoe]

So weird.

[Mary Elizabeth]

Oh, my God.

[Rachel Zoe]

I flew a lot of private planes. I remember that.

[Mary Elizabeth]

Oh, that's fun, though.

[Rachel Zoe]

I was on private planes. Very young. Very young.

[Mary Elizabeth]

Did you witness anyone have a total meltdown on a private plane?

[Rachel Zoe]

Of course I did.

[Mary Elizabeth]

Spill it. Who?

[Rachel Zoe]

Nope.

[Mary Elizabeth]

Who?

[Rachel Zoe]

Never.

[Mary Elizabeth]

Who?

[Rachel Zoe]

Honey. I witnessed more meltdowns between 98 or 97 and 2000. 8. 7 12. My wheels are turning 2013. My styling life is filled with milk.

[Mary Elizabeth]

We're at our time for today. You have just queued us up for Part two Meltdowns.

[Rachel Zoe]

Yeah.

[Mary Elizabeth]

So stay tuned.

[Rachel Zoe]

Part two of this podcast the Meltdown episode the Meltdowns.

[Mary Elizabeth]

Thanks for listening everyone.

[Rachel Zoe]

All right everybody, thank you so much for listening to Climbing in Heels. If you haven't already, please subscribe to the show on Apple Podcast, Spotify, the Iheart apps or wherever you get your podcast. You don't miss a single episode this season and be sure to follow me on Instagram at Rachelzo and of course the show at Climbing in Heels Pod for the latest episodes and updates. I will talk to you so soon and have a great week. You don't want vacation to end, but with Amex Platinum you're already planning the next one because you earn five times membership rewards points on prepaid hotels and more booked through amextravel.com so every trip to the beach and the city and the country and back home again leads to another destination. That's the powerful backing of American Express. Terms apply. Learn [e-mail] withamx it's sandal season at Dansco.

[Ryan]

That's right, Dansko, the iconic clog brand now offers sandals. Whether you're looking for stylish wedges, comfy flats or trendy cork sandals, dance Go has you covered. And don't miss the all new Platform Pro cloud. Visit Dansko D A N-S-K-O.com forward/radio to explore Dansko's full range of supportive and fashionable footwear. From Dansko's iconic heritage clogs to the latest designs. Dansko's easy to wear slip ons and adjustable styles are made to support you through even the busiest days. Plus enjoy free shipping and returns. Visit Dansko D A N-S-K-O.com radio today.

[Radhi Devlukia]

This is Radhi Devlukia from a really Good Cry. Did you know that approximately one in three Americans have insulin resistance and consume over 300% more than their daily recommended intake of sugar? Have you been wanting to beat your sugar cravings? Well I did a 30 day sugar fast and I found Apothecary Sugarcake that helped me through it. Their potent tincture features Japanese inspired ingredients studied for their ability to support healthy blood sugar levels, giving you more energy, less fatigue and fortified longevity. Find Apothecary in Sprouts farmers market stores nationwide and online@ Ulta.com, amazon and Apothecary.com. that's Apothecary with a [e-mail] when it comes to your health and well being. The right care can change everything. That's why Cleveland Clinic has been elevating world class patient care for over a century. From the latest in heart neurology and cancer care to advanced diagnostics and beyond, Cleveland Clinic is here for every care in the world. Explore a wide variety of health and wellness info by visiting clevelandclinic.org today.