← Her Style Podcast | Shopping, Color Palettes, Fashion, Wardrobe, Outfits, Clothing
Her Style Podcast | Shopping, Color Palettes, Fashion, Wardrobe, Outfits, Clothing
230 | The Secret to a Wardrobe That Really Works for You — with HER Style Collective Member Jenna Anderson
00:29:53
Surprise, surprise… I have a very special bonus episode for you today! This is not our typical Q&A Thursday conversation. Instead, I invited HER Style Collective member, Jenna Anderson, to join me for a very open dialogue about how she has...
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- [00:00]
Heather Riggs
Surprise, surprise. I have a very special bonus episode for you today. This is not our typical Q and A Thursday conversation. Instead, I invited her Style Collective member, Jenna Anderson to join me for a very open dialogue about how she's navigated so many of the challenges I know you might be facing too. In this interview with Jenna, she opens up about struggling for years to figure out her personal style and what flatters her. She actually clarified that it was in fact a seven year battle, rather right after we stopped recording and how all of that changed after taking the leap to join her Style Collective. She also talks candidly about her weight loss journey and how she's built a wardrobe she loves even through weight fluctuations. Plus, she reveals why her husband keeps encouraging her to renew her membership in the program. And we dissect the secret to having a wardrobe that really works for you, friend. I cannot wait for you to hear this episode with Jenna. Welcome to her Style podcast where we're all about empowering you to show up and get dressed every day with confidence. I'm your host, Heather Riggs, a 15 year and counting certified image consultant and color specialist, ready to build a wardrobe and a personal style you love. Let's get started.
- [01:28]
Jenna Anderson
Hi Jenna, my sweet friend. I'm so glad that you're finally joining me on her Style podcast. I feel like it's about time because we've been working together since last July, right? It's been months and I have seen such tremendous growth in you and on your Style journey from then until now. And I just want to recap kind of the whole thing and it probably makes sense to start at the beginning if you want to tell us a little bit about yourself and anything from your life that would be helpful to know and how you found her style and got started on this journey in the first place.
- [02:02]
Sure, sure. So I'm 41, I live in Minnesota with my husband and my 7 year old daughter. And I live a very outdoorsy lifestyle here in Minnesota, living on a lake and fishing, boating, snow, skiing, all that kind of great stuff. And as long as I can remember, I have not liked clothing shopping, I have not liked dressing. A lot of my life has been spent just buying clothes that I don't like a couple of months later and buying new items for a vacation or a night out or whatever it might be because I just simply don't have anything to wear. And a couple of years ago I kind of decided I should address this like this is something that should be fixable. I should like how I present myself to the world every day. And so I started down the path of trying to figure this out, and I feel like I uncovered or turned over every stone possible. I did all kinds of different approaches that are out there, lots of different style quizzes, lots of different categorization and trying to figure out what kind of bone structure I have and what colors I should wear and all these things. And I was just floundering. Everything seemed to fail for me. At some point it might work for a little bit, but then I couldn't figure out how to make it work for certain types of clothing or for a season or for whatever it might be. And so I inevitably just kind of failed or gave up whatever that approach was over and over and over. And I found your style quiz on Pinterest, I guess now, probably about a year ago. And I was immediately drawn in. I think it was one of the. I've probably taken 50 style quizzes now, but that one really stuck out in that it was very quick. I remember it asked, what would you do with a windfall? And I said I'd put it in my 401k, which I really liked, because I liked that it was more than just physically what I like to look at, but also who I am. And I remember thinking that the results were really spot on. Even though it was so quick, I couldn't believe that it was that accurate and that it felt like the style that I got back was so specific to me. And so I started listening to your podcast, and I remember thinking that you had this thing that I see a lot of women have where they have, like, an eye for fashion. They're good at understanding proportions and all these things. And it's always been something that I just don't have. And it's very mysterious to me. And I just know something doesn't work for me, but I don't know why. And you would break down concepts into really specific pieces that I could understand. And I started to think, oh, this is. This is like nothing I've ever heard before. And I feel like I could actually learn enough to be able to figure this out if I just kind of dove in. And so that's what led me than to looking into the collective and what you offered. And I think I've actually pulled the trigger. When I listened to your podcast about, you were talking about your Craze band and how you had nowhere to put your mic because you were wearing dresses, and you were, like, saying that you wanted to wear dressy shorts so you'd have a place for the Mic and I thought she is on my wavelength, because so often something like that will totally derail me. And so hearing you talk about the practicality of it made me feel like you would get me and that you could help me work through all the different kind of practical and other issues that I feel like are often ignored, and it's difficult to kind of work through. So that's what I think made me finally pull the trigger and decide to join.
- [05:28]
Oh, my goodness, Jenna. I feel like I'm getting, like, emotional just hearing you talk about. I mean, what a gift to feel like style and understanding how to dress your body was something meant for other people. Like, you just couldn't get it. And then to break down that barrier and say, oh, wait, I just need someone to explain, explain it in a different way. To me, this is something that's available. I do have what it takes to style myself and feel confident in that. Like, just. That's such an incredible shift to have happened just from the podcast. And I'm so excited that you took the step to really go all in with this process and trust it completely. And you've been so amazing at just going for it and asking the questions that you need and raising your hand when you get stuck to get the support. And let's talk a little bit about that. So you mentioned your personal style and starting with the quiz, and I've seen a major transformation of your personal style from then until now, and we've worked through a couple of different seasons together, and I feel like we kind of rewrote the rules for you because we were getting stuck a couple times. So tell me from your perspective, what was it like really dialing in your signature style and especially being in Minnesota and having all the distinct seasons. I know that's been something that's been really unique to you and some of the other members as well, but let's navigate that a little bit and explain kind of how that unfolded for everyone.
- [06:49]
Sure. So if you aren't familiar with the collective, it has very specific steps that guide you through the process of, you know, figuring out what your colors are, what your patterns are, all these things. And you do a closet audit, and you then plan out your wardrobe. And it felt like it was very straightforward. For a very long time. I was just following the steps. Everything seemed to be going really smooth and very easy, and it felt like the progress was very linear. And I got to a point where I had outfits that I was posting in the collective everyone said were cute and things like that. And I Felt like they were sort of. They were, they were cute, but they weren't quite me, maybe. And. And a lot of times how that would sort of reveal itself is I might like how it looks in the morning, but a couple hours in I am feeling frumpy, I'm annoyed, I'm messing with things. I don't really want to wear my outfit the whole day. I want to take it off and change into something different. And I remember really at that point, not sure if I should tell you, because everyone else I felt like was just kind of continuously getting better and better, you know, and they were just kind of narrowing in on what they wanted. And when I looked at my outfits, they weren't bad. They were. They were cute and they were following all the rules we had talked about. But I remember after maybe a week or two thinking, I should just tell you, I guess. And I was so nervous on the group call where I finally did. And I was so surprised and happy with your response because you didn't seem fazed by it at all. You weren't like, you know, thrown off or defensive or anything like that. You were just like, let's work through this. And what we ended up doing was going back to the drawing board a little bit and looking at the time period, by the way, was January, I think December, January. So it was really getting cold. Talking like, you know, negative degrees. And a lot of the things I was wearing were really bright colored. They were like a little bit snug. They were all these things that didn't quite feel wintry to me. And so we went through and we made some new Pinterest boards. And what you actually had me do was not pin any clothing, but just pin images that felt like, cozy and what I think of as winter and what I aspire to. And from that, I think you pulled a subset of those and it ended up creating a different color palette that was more neutral and calm. And the other thing that we did was we had a one on one session. And I felt like we also worked through some of the logistical things. And again, this is where I felt so stuck about shoes. For example, that time of year. And we worked through what was wrong. And this is again where you're so good at breaking down things in a way that for me, I just felt very stuck. Like I can't figure out what shoes to wear in this time of year. And I remember I felt like a light bulb went off when you said, oh, what you're seeing is you need a shoe that has more visual Weight. And it was like, oh, yes. And from there on out, then I, you know, I bought a couple of Uggs. I bought a, you know, a knee high pair of boots and things like that. And it kind of unlocked everything else. And what I feel like from my perspective is that until that point, I feel like I got 80% of the way there. But it was that last 20% that made it feel like me. And from there on out, I feel like, like all winter I felt so cute in the clothes that I was wearing. And they felt like, so me, I had a lot of like, wide leg jeans and oversized sweaters, and none of them had the big loose cuffs. That was another thing that was driving me crazy. And it all just felt balanced and classy and very sophisticated, but also very comfortable. And that's when all of a sudden it started to feel like, oh, this is not just a style, it's my style. And. And it's funny. Cause I feel like, oh, man, I'm so glad I didn't stop at that point. Like, I'm glad I didn't give up or throw in the towel or be like, this isn't. This just isn't working for me. Because it was that last little leg of the race that I think made all the difference. And now I also feel like it gives me the confidence to say, if something's not working, I know that we can solve it. Whereas I didn't necessarily believe that before. I felt like you could just get stuck on a style thing and just like never figure it out and lose all momentum. And so seeing kind of the ability to work through that, especially when, like, now we're talking about some of the solutions. At the time, I didn't even know what the problem was. And that was maybe the most overwhelming part of it, was to just tell you it doesn't feel quite right and I don't know why. And I feel like you really helped me work through what the. And it was the various things, what all those little things together added up to and why it didn't feel like me.
- [11:15]
Wow, there's. I feel like there's so many things that you said that I really want to go back and touch on, but I feel like the overarching thing that I want people to take away from that is that when I say that this is a personalized approach, it's personalized whether we need to stop at step four and go back to step one for you to kind of re evaluate something that's maybe not working. If we need to take A detour and try something completely different. My goal is to make this program work for you in the way that you need it to work. So, yes, there are clear cut steps that you can revisit season after season. And Jenna, now that you've dialed in some of those missing pieces, I think you could confidently go back through the process from start to finish and just check every everything again for this summer or next fall or for life and use it as much as you need to. But yeah, I'm so glad that you brought those questions to the table because I can't coach you unless I know what needs to be coached. And so really, all your job is coming into this program is keeping an open mind, being open, and communicating your thoughts, your feelings, your concerns, your questions. And we can absolutely work through any of those challenges together. And that's the beauty of this, is that you don't have to figure it out on your own anymore. You have me and the collective team really there to not only hold you accountable, but also hold your hand through the process. So it doesn't have to be overwhelming. There's always a solution to everything. And it was so fun to also kind of come up with some new ideas for you of doing a whole style mood board that had nothing to do with fashion. And you were throwing family photos in there and outdoor images and interior design spaces. And we just got to be creative and play because sometimes that happens. You might be so busy, busy looking at inspiration from other people's outfits, but if your look is really distinct from that, it can be hard if you're not seeing exactly what you want on other people.
- [13:05]
Heather Riggs
So we just got to make it.
- [13:06]
Jenna Anderson
Up for you and really land in the perfect place. And another thing also to point out is that sometimes the way we want to look in the winter is very different from the way we want to look in the summer. And that's why I do say it's so important to reevaluate your style every so often. Maybe even just once or twice a year is really helpful to keep you on pulse. Thank you for sharing all of that. I would love to hear what other results you've had since coming into the program.
- [13:31]
Well, it's. It's honestly just life changing, to be totally honest. And again, for someone who's just been good at clothes their whole life, it might not seem like a huge deal, but getting ready for a vacation that I just took last week, for example, it was so great to go to my closet and to just feel like I had so many options And I had options that could mix and match. I had lots of things that were for different levels of formality, you know, whether it was a dressy dinner or being on the beach or whatever, to just feel like I had lots of choices. And in the last, you know, four to six months, I've had lots of, you know, date nights or meeting out with friends or whatever. And every single time, I had the, like, total joy of selecting what I want to wear versus feeling like I have. I have nothing. I'm just going to wear with something that fits, something that is stretchy, something that, you know, barely meets the mark. Instead, I actually get to say, you know, how do I want to feel? Do I want to be a little more dressy today? Do I want to be a little more casual? And I have just lots of options to support that. And some of that is also getting the little building blocks in place, you know, like, making sure I have lots of tops that can go underneath things so that I am comfortable in the winter. Just things like that that are small. Again, this is where I feel like you're very practical, which I appreciate, which is to really figure out all the different pieces that have to come together to feel confident. And it's, you know, having a bag that can fit my hat and mittens when I go to coffee and I have somewhere to put things. Like, all those little details matter, and it took a little bit to build them up. And now that I have them, it just feels like, oh, it's. It's a breeze getting ready. It's a breeze to just select. And it's. It's part of the fun, I think, of being a human to say, what do I want to wear today? How do I want to present myself? And I felt like for so many years, I just didn't have that luxury. And so I just kind of feel like a kid in a Tony store a little bit getting to do that. So it really is life changing.
- [15:20]
Heather Riggs
Hey, friend. I'm sorry to interrupt this conversation with Jenna, but I have two very exciting updates to share with you. First, if you're listening to this episode, the Day it airs, on April 10, 2025, we are just about halfway through our first ever completely free shop your closet challenge. And if you're not registered yet, you still have time to catch up. The replays are available all week long. So if you're ready to get out of your wardrobe rut and start putting together better outfits with what you already own, then I want you to head to herstylellc.comchallenge to hop in with us right now. When it comes to an event here at Her Style, you are always welcome to arrive fashionably late and if you are feeling inspired by Jenna's story and you can relate to her struggle of desperately trying to figure out what flatters you, of wanting a wardrobe that actually works for your life. Of having the desire to feel confident, stylish and put together without overthinking it. If you are overwhelmed and you want clear cut steps and a personalized approach to help you figure this out once and for all, then I want to let you know that we're offering a very special challenge week savings and bonuses on Her Style collective this week only. When you join us for this 90 day group coaching program by Sunday, April 13th, you will save $100 on either the one time investment or the affordable payment plan and you get a whole bunch of incredible bonuses to support you on your journey. I don't want you to miss out on this opportunity to transform your wardrobe and the way you think about shopping and getting dressed. If you've been on the fence about stepping into this program, this is the nudge you've been waiting for. It is time, friend. Let's team up to get you feeling confident and put together every single day. You can visit herstylellc.com challengesavings to get all the details and to join us inside with the limited time Challenge week savings and bonuses available through Sunday, April 13, 2025. We're ready and waiting for you. I'll see you inside.
- [17:26]
Jenna Anderson
The other thing that I think is probably even more profound and what I really care about as a mom especially is I want my daughter to see that I love myself and that I feel confident in who I am and presenting myself to the world. And so there were also several things that I just thought I couldn't wear. Like I've not worn shorts in, I don't know, 10 years. And you helped me realize that I can wear shorts. I just have to find the right shorts. Also, certain styles of clothing we've kind of had to work through the mental barrier of ordering something that is a bigger size than I perhaps want so that I can then get it tailored to really fit me really well. That was a huge mental barrier to work through. But once I have now, it's so freeing to say I can look good regardless of my size, regardless of my weight, I can wear whatever I want. I just have to find the right things. And it really just means fundamentally, at the deepest level, there's nothing wrong with My body, it's just about finding things at work. And that is just a very freeing and empowering feeling. And something, like I said, that I want my daughter to see. So that has been a huge, huge, just mental shift.
- [18:26]
Overall, those are my two biggest goals for anyone coming into this program. That the first part of what you were talking about was that it sounds like you have a wardrobe you love now and it is a joy to get dressed. And the other part of the equation is that you feel confident in who you are today and you can show up that way and reflect that for your daughter and set an example for her of speaking kindly to yourself and feeling good in your body and embracing where you are. And that is such a gift not only to you, but to her, too. So that's incredibly exciting to hear all of those things. And you have been very transparent too, from the beginning. You, I think, came into the program and saying that you were on a weight loss journey. And I know we've talked so much.
- [19:09]
Heather Riggs
In the group on the podcast at.
- [19:11]
Jenna Anderson
The Shop your Closet challenge this week about how as women, our weight fluctuates. It really does. And I know for a lot of people I hear, I really want to do this, but I need to lose X amount first or I need to get my postpartum body back or whatever the case might be. We do sometimes have those hang ups. So I'd love if you're open to talking about how has kind of some fluctuations because we've been working together for a while. Right. And how has some of that been for you? And how have you navigated applying what you've learned through the program and working with what's in your closet through some of those different ups and downs that you've experienced, like all of us do.
- [19:47]
Yeah, So I did definitely lose weight in the first part of it. And unfortunately I got sick a couple months ago and so I put back on ten pounds. So I've kind of gone the the gamut here, if you will. And I definitely also had the feeling before I joined the collective, I thought to look cute. I probably can't look cute unless I'm my ideal route, which by the way, is, you know, in my mind, the ideal is like this unattainable thing that, you know, I'm a curvy person. I've never been like a stick thin girl. And so when you look on Pinterest, a lot of pictures are just completely unattainable. It's never going to be what I look like. And so to see that is really disheartening. And to feel like that's the only way to be cute is very, very. It's very frustrating. And so I did just really have to sort of, like, plug my nose and be like, I deserve to feel good right now, and I'm going to join the collective, even though I'd like to lose 20 pounds. Like, that was kind of my. My thinking, and I'm so glad I did, because honestly, it doesn't matter, like, now that I really step back from it, like, you can look good at any shape, but I didn't believe it at the time. So I'm so glad I just joined. And in terms of, like, how I've managed the weight fluctuations, this is where, Heather, you might have to share how it is for other people. But, like, I kind of have a look that I like oversized. I like that kind of baggier, looser look. And so I maybe has been somewhat of an accident, but I have found that the clothing that we have found for me has mostly fit regardless of the weight fluctuations. To be honest, going up or down, I mean, it's probably been a difference of £25 now in total. It hasn't really changed a lot of how a lot of the things fit that I've purchased. I will say I do lean towards where I gain weight is my bottom half. That's. That's my body type is a pair, and I forget what the term uses. And so, you know, pants can be very difficult. But I think what is also flattering to the body shape is a lot of wide leg options. And so a lot of those things still fit. You know, I have them tailored now to my waist, and, you know, so they're. They're fitting snugly where they should, and then I feel like there is give. And so, you know, I was a little worried when I was getting ready for my cruise because I had gone up 10 pounds, but I tried on everything, and it all still fit really well. And I. I will say I lean toward more stretchy materials. All the jeans that I bought mostly have some kind of give. And so there is. There is some fluctuation there. And I have known that if I do, you know, lose the £15 I'd like and a couple of things don't fit, then I might have to reevaluate those couple of things. But that's been kind of like a happy surprise to me. And I don't know if that surprises you that a lot of the things I think I naturally gravitated to have that that gives, and that's really worked well.
- [22:31]
It doesn't surprise me, and I think it's fantastic. And I think probably what we also want to point out, too, is that the basic foundations that you learn through the program don't change no matter what your weight is. Right. Like, your shape is your shape, and the that are going to flatter you best in terms of silhouettes and fabrics and prints. And all of those things are what they are. If you go up, you know, 10, 20, 30 pounds, it doesn't really impact how you dress your body. It may impact the size of the clothing that you wear. You may need to have things taken in a little bit, or you may want to opt for more of the stretchy fabrics that you have in your closet, those kinds of things. But everything you've learned doesn't go out the window. You get to carry that.
- [23:08]
And that's a good answer.
- [23:10]
Yeah. And I think it really depends on the specific person, what styles you like. If you are someone who's more inclined towards really fitted pieces or really structured things, we might need to work with that a little bit differently. We also share tons of tips on how to make clothing work better for you if it's a little too big or too small in the shop your closet challenge this week. So you can still go back and watch the replays of that if you want some tips beyond just Jenna's lucky nature of her styles. Really accommodating for that. But that's amazing that you've really been able to just kind of keep riding the waves and feeling your best every single day, no matter your size. I love that so much. And, Jenna, I just. I think I really want to close out our conversation by is there anything else that you want to share about the experience or maybe anything that surprised you coming into this program and what you would tell anyone who's really on the fence or considering jumping in with us.
- [24:01]
This week, I think the biggest surprise, I was the community, so I was very hesitant to do Facebook. I don't know if you remember that back in the day, but I was like, I'm just going to email you. I don't want to go on Facebook. I'm not. I'm not even on Facebook personally. But I ended up sharing, and the friendships that I felt, like, really developed were just very surprising and very, very heartening. It was really sweet. I mean, I feel very, like, very affectionate toward Ginny and Neva and Amberly and the people that kind of went through it. At the same time, as Me, I'll never forget seeing Neva in her beautiful silver dress for her solo. And just, like, I'm just so proud of her and so excited to see her, you know, looking for this absolute best. And so that. That ability to kind of make friends with people all over the world that are doing different things and different parts of the journey, I think was just a lovely surprise. I think we all were really supportive of each other. So I feel. I feel really lucky to that. I think that was a nice. Like, a bonus almost, is to meet these other women. And then in terms of advice I would give, I mean, I would just say to jump in is the first thing. Like, regardless of if you feel like you need to lose weight or do anything else, like, just jump in. And then I think it's to really commit to doing it all the way. I think it's easy to kind of, like, do it for three months and feel like, oh, okay, now I've got what I can, or I've hit a plateau. I think you do hit plateaus along this journey, and things will change. Like, you're. I think you'll either hit a different season or you will get deeper into your own style, and you'll have this ability to kind of hone more and more and more the longer you commit. And, like, at this point, I feel like I largely have what I need, but I know for summer, all of a sudden I might have a couple new things that I need to figure out, or I just joined a dance class and I wanted help on how to dress for that. Like, there's new things that'll come up. And I think that saying I'm going to really commit for a longer period of time allows you to get past that plateau, to really get to your personal style. And I'm just. I'm so grateful that you kind of, like, hung in there with me while I was sort of. I kind of went down and I was. I was not sure where to go. But kind of getting past that is where I feel like the true magic happened. And so I don't know if that's everyone's experience, but if you hit that point of pushback, you know, where you feel like you're a little stuck, I think that's. That's where, if you can dig in, the true magic will happen always.
- [26:24]
I'm always here for you. And I will say, anytime that you are in the trench, if you just reach your hand up, I'll be there to grab it. I just need you to reach for it and Let me know what you need, and we'll figure it out together, like we said. Yeah. And what's great is you can go through the whole process and really focus in on three months, and life's gonna happen. I think for every single member that's gone through the collective, something has gotten in the way, Some obstacle has come up, something has pulled their focus out. And the number of times I hear, I'm so sorry I haven't been on the calls in a couple weeks or life got busy. It's like the program is really set up for that. It's not meant to be your whole focus. It's there to help you live your best life and show up for all of those great things and to not have to worry about getting dressed on top of it all, because we have enough stress and worries as women. We don't need that to be another one of them. So there is a lot of kind of time and space and support built into getting you through it, even when life gets in the way. But it's so great when you can renew with the membership option, either right away, or you can always come back and jump in with us for another season if you need a quick refresh. But like you said, I think on the process, you're. You're kind of up leveling. So where you are three months after you start is so different from where you began. But then you're looking at, okay, now what's next? There's always opportunity to continue growing and refining and calling your wardrobe further and maybe shopping for those last couple pieces that you need. So while we can get so much done and really help you feel amazing in your wardrobe in three months, it's just exponentially more that we can do as we continue. So I love that you've been all in and ready to keep kind of doing the work and at least for a full year, really getting your wardrobe kind of dialed in for every season. And just to speak to the Facebook thing, I did not remember that you were one of the ones that didn't want to be in there, But I hear that a lot. They're like, I don't do Facebook. Some people never come in. And that's totally fine. It's definitely an option. But I feel like nine times out of 10, people get pulled in by the amazing community that we have and seeing everybody on the weekly calls and just wanting to be able to be there to support one another through it. So I'm glad you jumped in with us, and I'm so glad that we get to keep working together. And Jenna, thank you for your time and sharing so openly about your experience and all the incredible results that you've had over the last few months. I'm so proud of you.
- [28:38]
Oh, thank you Heather. It's great. And I should say, my husband also totally supports me every time we talk about renewing because he's so grateful that I can raise my hand and go to Heather when I'm stuck. So I think it's one of those things where your loved ones see you struggling and to just know that you have a phone, a friend, is a huge thing to know that you've got that support. So I appreciate it all. So anytime you'd like me to talk about my experience, I'm happy to.
- [29:02]
Thank you friend. I appreciate you so much.
- [29:06]
Heather Riggs
Thank you for listening to today's episode. If you want to stop copying everyone else's style and start dialing in your own swoon worthy signature look, head over to take my free 5 minute personal style quiz which you can find at the link in the show notes. If you've enjoyed our time together, please be sure to rate, review and subscribe to her style podcast so you never miss an episode. Finally, I invite you to make this a two way conversation and send me a DM over on Instagram eatherriggstyle to let me know how I can best support you on your style journey. I'm always here for you in style and service. Until next time.