You’re reading the second-to-last episode of Season One of Intuitive Style. While we’re on break for summer, you can catch up with all of the incredible previous guest episodes here. Next week, we be our season finale with mindful living extraordinaire Christine Platt. Stay tuned!

I’m delighted to share this week’s episode with much-awaited guest, Jennifer Cook of mom friend! We discuss everything from how Jennifer’s professional experience in fashion impacts her personal style to what she most enjoys writing for Substack! Enjoy.

Episode Transcript

This transcript has been edited for clarity.

Maureen: You're listening to Intuitive Style, where we believe that everyone has style. I'm Maureen. In conversation with fantastic guests, we explore how to tap into our style intuition so that we can dress authentically and live fully. Today's guest is Jennifer Cook from mom friend. Jennifer is a Brooklynite with a job in fashion. Chic. You know her from her weekly recaps covering everything from what's happening in politics to what the moms are wearing at Space Club. Jennifer, welcome to the show.

Jennifer: Thank you so much for having me. It's so nice to meet you.

Maureen: Likewise, I've been reading mom friend for a little while. I'm not even a mom and what you're writing is still really interesting from the fashion insider perspective—just like life in Brooklyn. I like catching up with what Mom Friend's up to.

I took a look at your about page and it really struck me. You said, “when something becomes your job and pays your rent, it's easy to become numb to it. This page has helped relight my curiosity and interest around the industry as a whole, and I love being able to write about it and be in it at the same time.” I don't work in fashion even a little bit, so I would just love to hear a little bit more about your day job in fashion and how writing in your free time feels different.

Jennifer: Yeah, I have been working in the fashion industry on the business side for about thirteen years now. I started on the retail side when I was like fifteen, so I've always been around retail and fashion. It's just kind of ingrained in my bones and who I am. But that said, when you work in something, it becomes a little monotonous. Or when it becomes your paycheck and your livelihood, it can kind of lose some of the luster.

Part of the reason I got into fashion was because I loved it. I loved the clothes. I loved retail. I loved the energy it brought. I loved the people, the artistry, the creativeness of it. Being on the business side for the last decade plus, it lost a little bit of its luster. So in writing the Substack and developing mom friend, it's been so fun to kind of find that playfulness again where it's not so dependent on—my livelihood is not dependent on it. I can play with it, I can have fun, I can explore, I can learn, I can engage with it in a way that's a little bit different from my nine to five.

In the last year or so, I started a new job. I'm a buyer now at a store in Soho in New York City, and I like to laugh about it and say that I just shop with someone else's money for a living, which is not super far off from the truth. But it still has that expectation that you're doing it for someone else—for a store with a different personality, a different customer, a different viewpoint. So on the Substack, it's fun for me to just do things for me. It's what I like. It's what I'm finding. It's what I'm resonating with as opposed to what I'm getting paid to find for someone else. That part has been a lot of fun.

Maureen: That's a really clear and powerful distinction. When you're shopping for the retailer, it's not necessarily about your taste. It's also about what is going to sell, right? Just based off of some things that I've read from you. Is that kind of a fair shake?

Jennifer: Absolutely. There's so much data these days behind my job. So it is kind of a gut feeling you have. It's a taste level. It's knowing your customer. But it's also looking at metrics like selling and developing merchandising plans based on how many iterations of a short sleeve you might need. It's looking at profit margins. These days, where it's being made and where it's shipping from is all the more important. So there's so many factors that come into how I'm buying for the store versus how I look at fashion and style just for myself.

I've been lucky in this role. I've been able to bring a lot of my own personal taste and style and preferences into it. So I feel very fortunate that that's been afforded to me. But at the same time, there's so many other things that go into that job that are based on data and numbers and metrics and getting to know a different customer than I am.

Our store is in Soho, New York. I live in Brooklyn. For those not in New York, those two things are worlds away from one another. The style that you see in Brooklyn and the style of people roaming around Soho—it's vastly different, even being just a few miles apart. So it's really interesting to have to kind of capture that information, process it, and then feed it back in a different way through the store and through my own style.

Maureen: Totally cool if this is too much information from your company perspective, but what is your customer base like then for the brand?

Jennifer: We started many years ago as a menswear brand. So our core customer is a guy. I kind of call him the LinkedIn bro of New York. You know the type—he's a corporate bro, he likes nice things, he's an aspirational customer. He's not totally buying luxury, but he's also not shopping at Zara. He wants things that feel good, that look good, that are basic and easy to wear and don't take a lot of styling. That's always been our core customer.

In the last year, we've transitioned into becoming more of a multi-brand concept store. So we now have women's apparel, home goods, accessories, footwear. It's been a lesson in trying to figure out who that new customer is and how we get new people in the door.

Being where we are in Soho, it is also very tourist-driven. It's striking that right balance between basics, vacation clothes, and fun grab-and-go items for people to remember their trip by. It really spans a wide range of customers. But it's also ever-changing. Especially in New York City—it's such a transient city. People are coming, they're going, they're changing jobs, they're having families, they're moving to Brooklyn. There's always change in who our people are. It's been fun over the last year to try and identify that and not just give them what they want, but also try and tell them what we think they should want. It's striking that balance between things we know they'll love and things we think they should be following. It's a hard balance to strike, but it's also really fun.

Maureen: And I know that this line of questioning could seem tangential to your personal style. But for me, it helps me really understand where you're coming from and how you could get to that place where fashion is a little bit less fun. Everything you're describing sounds very cool and also very corporate. There's a connection element to knowing what your customer likes, but also very business-oriented. Going back to what originally drew you to fashion being the actual clothes and the experience of clothing—those feel worlds apart. What do you think your day job in fashion is? What is the impact of that on how you personally dress, if anything?

Jennifer: It's a huge impact. Less so in my current job, but previously—before becoming a buyer—I was working on the wholesale side of the business where I was representing individual brands. Every time I would represent a brand, I would kind of have to dress in that style. I would dress in their clothes pretty much head to toe. Part of that was due to the fact that I usually had a nice allowance or got a steep discount, so it made it easier to dress like that. One of the perks of the job for sure.

But part of that was also—you feel like a representative of that brand. I always felt like I needed to dress the part in order to sell it better and do my job better. Now that I'm on the buying side, I have a wider breadth of options to choose from, which is great. But on the other hand, there's so much out there that I almost feel too inundated with products sometimes. I'm looking at all these amazing products from hundreds of brands and it can be decision fatigue and information overload. It's been a lesson in trying to pare back my own style and see what resonates with me. What do I actually feel good in? What do I want to wear that fits my life?

I'm looking at all these amazing products from hundreds of brands and it can be decision fatigue and information overload. It's been a lesson in trying to pare back my own style and see what resonates with me. What do I actually feel good in? What do I want to wear that fits my life?

Part of my Substack is talking about fashion and how it relates to the life I actually live. I'm a newish mom. I have a toddler. I live in Brooklyn. I'm on my feet all the time. I'm always running around. I'm also a yoga teacher. I'm writing. All of these things play into the way I want to dress. And that's not really what I'm selling in my store necessarily. I need my clothes to work for me. I need them to be washable and easy to wear. I need sneakers. I need really basic things. I live in Brooklyn. I have a small closet. I don't have space. How can I get the most out of my clothes?

Sometimes I feel lucky to be able to buy things for the store that I can't buy for myself because they don't fit my lifestyle. It's still a nice way to work with younger brands and designers, get them out there, without having to take on—not that it's a burden—but that burden myself of owning their product. It all plays together for sure.

On the other hand, I'm out in the market all the time and sometimes I see amazing pieces that I’m like, I don’t care if I’ll ever get use out of this. I have to have it. I have to support this person. I need to have this brand in my closet. You just fall in love with things.

That also said, if anyone’s worked in retail, you probably have experienced wanting something when it first hits the floor and three weeks later, absolutely not wanting to look at it ever again. So there are pieces I fall in love with that after three weeks I’m like, you know what—never mind. I actually don’t need this.

So it all plays together. It’s been a lot more fun in this new role having exposure to multiple brands and not feeling so set on dressing as one brand or one style. That’s been a lot of fun to play with. But it’s also lined up with having a kid, which just totally flipped my wardrobe on its head.

Maureen: Yeah. Well, we can talk a little bit more about that. And I also want to see what you think of this idea. So personally, I always have resonated more with what the designers are wearing than the actual clothes that go down the runway. And just based on, you know, like the chic black crew neck that you're wearing today and just other things that you share. And even just the lifestyle that you're describing that is more... like, our clothes need to be more utilitarian than always expressive and I feel like, I'm just curious, do you resonate with the designer style? Is that something, do you ever think about that?

Jennifer: Always, always resonate with the designer style more than the clothes that go down the runway. These designers work hard. They're crazy busy. The women are, tend to be the ones that I follow most closely and most of them are moms. They have a lot of things going on. It's like me where you need to pare down your style and really keep it simple. I think there is something to be said about uniform dressing or capsule dressing or however you want to call it. That keeps having these small moments in the conversation and there is something to be said about that. It makes the getting dressed part of your life a little bit simpler so that you can focus on the work of creativity. And I think that is why designers tend to have a little bit, in my opinion, more of an interesting style—something that I resonate with a little bit more. Not that I don't love looking at the runway clothes.

Always, always resonate with the designer style more than the clothes that go down the runway. These designers work hard. They're crazy busy. The women are, tend to be the ones that I follow most closely and most of them are moms. They have a lot of things going on. It's like me where you need to pare down your style and really keep it simple.

Maureen: Oh, yeah.

Jennifer: I think they're beautiful and they can be super creative and amazing, and the construction on some of them is just incredible. But at the end of the day, no one's wearing that, right? It's a marketing tool. These runway shows are marketing tools. And working on the wholesale side of the business, I know that most of what goes down the runway doesn't make it into stores. There's a whole other collection that these designers design that are made for retailers, that are made for people to actually buy. And that's not what you see on the runways. And so there's this whole other kind of underbelly of the industry that I feel closer with. And that includes dressing like the designers. They also just—they're amazing. They know what they're doing. They know how to dress their body. They know about proportions. It's so fun to watch them come out at the end because I'm like, okay, that's what I want to wear.

Maureen: Yeah, same, same. Sometimes I feel like getting dressed super expressively can be a distraction from life. And so I feel like, yeah, if you imagined, like, Pier Paolo wearing super... what if he wore gowns or something in his day-to-day life? Would we take him as seriously? Because if you think about all the hours of glam or whatever he'd need to do to get to that place, wouldn't that take away from the time that he would need to be creative or to actually work on the designs? You know what I mean?

Jennifer: Yeah, that and we live in an attention economy. And so when your attention becomes on yourself, when you start to make yourself the brand, when you start to dress in a certain type of way or put yourself out there in a certain type of way, then you become what people pay attention to. And I think designers know—some of them at least—that the attention needs to be on the clothes. It needs to be on the product, not themselves. Granted, it's hard to have a successful brand these days without a face behind it. So it's striking the right balance between those two things.

But, you know, being in New York City too, it's average people. I take the subway multiple times a day and you can tell the people who are on the subway that are going somewhere where their job is their clothes or their job is to show off or they're trying to get attention or whatever it may be versus the people that are there on their way to the office. They have stuff to do. There is this dichotomy between people just walking around the city streets—the ones that want to be seen and that show off, and the ones that are there to work. And there's nothing wrong with either of those things.

Maureen: Total, yeah.

Jennifer: It's just what you think about when you get on in the morning. And I am not one of those people where I want to be seen. I don't. I don't want any attention. I want to just keep moving on with my day. And so I definitely dress for that. I want to blend in. But I also really appreciate the people that don't. I think it's so fun. I mean, the city streets are just a constant source of inspiration. So it's fun to walk around and observe that. But I do think we live in a society that feeds off of attention these days, and so it's just what kind of attention you want to bring to yourself. And our clothes speak volumes.

Maureen: Thanks for going there with me. And of course, I would never try to get you to say anything bad about dressing more expressively, right? I think everyone has—there’s a space for every kind of dressing.

Jennifer: Yeah.

Maureen: And the only reason I was asking is just I felt like that's something that resonated with me about your style, is that I also kind of am personally more comfortable being a little bit more reserved with my style.

Jennifer: Thank you.

Maureen: And I think when you focus a lot of your energy in the fashion space on what’s going down the runway and things like that—certainly I can just say for myself—I felt a lot of pressure to be that flamingo, to be the peacock and do the most, and that I wasn't stylish if I wasn't doing the most. And so that's why paying attention to what the designers are wearing and even just, you know, what you're putting out there helps me be like, “Oh, I can be a fashionable person or stylish person and also wear things that are more subdued.” So that's really, I think it's nice to make space for all the different types of dressing.

Jennifer: Absolutely. And I used to be that person too. I mean, when I was younger, dressed to the nines, I was always in heels and tight dresses. And I think as my life has progressed and my day-to-day has changed and my situation has evolved, those things have changed as well. And so I think everything has a season and a place and time. Ultimately, style just comes down to feeling good in what you're wearing. And if that is a basic black sweater and jeans—great. If that's a mini skirt and bra and high heels—great. If you're happy, I'm happy. That’s what matters.

Maureen: I completely agree. I have one more mom friend question before we get into your personal style.

Jennifer: Totally.

Maureen: I really appreciate that your posts are labeled with the number at the start because it helps me remember when I'm reading that you have a large archive of posts. You were writing for a little while before I found you, and so I can go back and read your past work. With that said, are there any memorable favorites or underrated posts that you've written and are proud of? I'd love to know about them.

Jennifer: You know, it's not that there is a specific post necessarily. I think a couple of things. First, my writing has evolved. I've been doing this for about a year now, and what it started as to what it is now is totally different. If you go all the way back to the beginning, it's just a different beast. It was more me trying to find my way as a new mom, so a lot of it was more personal essay-centric or parenting products or conversations around that. And as I've developed it and gotten used to writing, and as I've kind of grown with it, it's morphed into a lot of different things—more focused on just me and my personal style as well as politics. There's still some parenting and motherhood content, but it's a little more well-rounded.

There are some great pieces that I wrote that were more personal essays a year ago when I was just starting out and I had like two followers, and I felt more comfortable just kind of putting it all out there on the internet. But on the other hand, part of the reason it's changed is because I realized what was gaining more traction and what people wanted to read. And as much as my goal is not to just pander to my audience, I do also want to know what they're interested in. I feel like I have a very specific viewpoint—working in fashion, being in New York City, being a mom—I think those are things that people are curious about. As people started to express more about what they wanted to hear and read, I started catering to that a bit.

[Ed note: issue #60, a week in Jennifer Cook’s life in Brooklyn, is the first one of hers I read, and I was immediately hooked.]

So it's developed along with my audience. I don't necessarily think there's anything super underrated that I want people to go back and revisit. It's more just giving ourselves permission to evolve as we move, as we wish. Some of that is audience-directed. I also found that I didn’t want to write about fashion—I really didn’t—because I worked in it. But as I started doing it, I realized I actually enjoyed writing about it. This is what I do. This is what I love. I've been doing this for a really long time. So of course I like it. I realized I shouldn't hold myself back because I originally started with the plan not to talk about it.

I also realized that I have no idea what I’m doing when it comes to being a mom. I got a few posts out about parenting and motherhood and then I was like, okay, that’s it—that’s the end of my knowledge. I can’t keep going with this. I have to expand it, because otherwise it's like the blind leading the blind. I have no idea what I’m doing. And I think that’s part of the fun—it’s an exploration of how I can be a mom in this world, in community with other people, while also acknowledging that there are so many other aspects to us as individuals. "Mom" is part of it, and as I continue to write, I realized that all of these other parts of me—I wanted to explore and share those too.

I think it's interesting to see what people gravitate towards. My Substack has become very shopping-centric, and that’s what people really like to read. It definitely gets the most engagement. What I like to write and what I’m most proud of tend to be the least engaged-with posts—the more personal things, the more political things. That’s why I started doing the weekly recaps on Thursdays, because it allowed me to explore the things that I’m more excited about. Not that I’m not excited about shopping and such, but I feel like I am very multifaceted and I like to put all of that out there in one place. And those are so fun for me to write, even though they’re not nearly as engaged with.

Maureen: As another creator, I really appreciate you sharing all that detail about what people are reading, because I've also experienced the same thing. The more specific I am about clothing, the more people want to engage with it. And when I try to do things that are a little more—what's the word—philosophical or esoteric or thoughtful, then I'm writing for the writers.

Jennifer: Yeah.

Maureen: And that's totally fine, but I think sometimes there can be this misnomer, like if you write what's authentic and organic to you, then that’s going to be the most popular stuff. And it's like—well, sometimes not. And then sometimes people just want a roundup of all the cute dresses that you’re buying for summer. And that’s totally fine.

Jennifer: And that’s kind of the content I like to consume too, because the world is heavy right now. Reading personal essay after personal essay can also be heavy. Sometimes we need a break and just want to look at pretty things. There’s nothing wrong with that. For me, I want that, and I also want to be thoughtful and put things out there. And if people read it—great. If they don’t—fine. It’s whatever.

Maureen: Everything that you described is a lovely analogy for the idea of intuitive style, which is basically: we're trying stuff out, we're seeing what feels good to wear, what feels good to write, what people are interested in reading. It’s all kind of a micro-experiment, one post at a time. Let’s talk a little bit about your personal style. How do you decide what to buy and wear, especially given that, as you said, you are so inundated with great options? How do you pick?

Jennifer: It’s hard. There’s so much good stuff out there—it’s so hard. For me, the biggest things are that my body has changed a lot in the last couple of years—being pregnant, giving birth, and then everything after that. So that’s been a huge development in my personal style lately. It’s a major part of it.

I am a notorious outfit repeater. I tend to wear a variation of the same thing every day, mostly for ease. I am very busy. I’m very tired. And to be able to just throw on a combination of the same thing makes my life a thousand times easier. So even though everyone says don’t buy duplicates of the same thing in different colors—I definitely do. If I find something that fits, that I love, that I wear a lot, and that’s in my budget—I'm buying it.

Budget is a major factor for me. Fashion pays notoriously low. I get access to a lot of great discounts, which is amazing, but I am very conscientious about what I spend on clothes. I have a lot of expenses in my life. New York is an expensive city. Unfortunately for me, clothes kind of fall off when it comes to spending. I also have enough. So when I’m trying to figure out what to buy, it’s mostly about filling in holes in my wardrobe.

Lately, that’s been pants and jeans, because my body has changed and a lot of things I had pre-baby don’t fit anymore. So my priority has been making sure I have bottoms that fit and feel good. Right now I’m in the market for the perfect gray sweater, and I’m not going to stop until I find one that’s in my budget, fits really well, and is the perfect color. I’m comfortable waiting until I find that one that really works.

There are so many factors at play in deciding what to buy. I also have a few go-to brands that I’m consistent with—I know they fit well and I can buy them easily. I stock up on things like white tees and similar staples. But every day at work, I get line sheets from apparel brands and I’m like, “Damn, I want all of this. How do I choose?”

More recently, with everything going on in the world, I’ve tried to make a point of buying from women-owned brands and those that focus more on slow production and ethical practices. I’m trying to be more conscientious about that. Don’t get me wrong—my daughter pretty much exclusively wears H&M and this sweater is from Gap. So I’ve definitely got mass market in the mix. But when I’m thinking about a bigger purchase or spending more money, I want it to be more meaningful.

As I’ve gotten older and had a little more room to play in terms of budget, that’s been huge. I’m also a big Poshmarker. I love secondhand shopping on Poshmark. If I find something I love but don’t want to pay full price or am unsure about the fit or how often I’ll wear it, that’s a great resource too.

Maureen: Yeah, I feel like Poshmark is great, especially if you use it to buy something you already know you like and just want another one of. Do you ever use it that way?

Jennifer: All the time. Yeah, that's great.

Maureen: It's pretty no regrets if you're like, “I already have it and want to re-purchase secondhand.” Cool. It sounds like a heightened version of what a lot of us are feeling, which is: How do you pick? How do you pick? How do you pick? And then there are so many people doing the valiant work of trying to de-influence, and sometimes it turns into a very loud voice saying we don't need things—when maybe we actually do have gaps in our wardrobe. I find that can be kind of distracting for me personally. I appreciate that your writing doesn’t skew that way. I think you leave room for all the different ways someone might shop, and I just appreciate that.

Jennifer: Oh, good. I'm so glad. I mean, listen, we all need less stuff. I think we generally consume too much. But at the end of the day, we want to feel good, we want to look good, we want to be comfortable, and that sometimes requires shopping and buying. Whatever your budget or price range may be, there's something for you. I never want people to feel bad about spending money to make themselves feel good—especially when things are not so amazing right now. Clothes bring me joy, and retail therapy is a real thing. I don't think we should be running away from that. I want us to be conscientious about what we're consuming. We could all take a closer look at our spending habits and our shopping habits. If we're just throwing stuff away or buying things we don't need just to feel that endorphin rush, then yeah, we need to pay attention to that. It’s important, because there are serious problems with the way Americans—and not just Americans—consume. But at the end of the day, if you want the damn jeans, buy the damn jeans. Are you going to feel good? Are they going to make you happy? Are you going to wear them? Then hell yeah. Why not?

I tried really hard to do a no-buy 2025, and that ship sailed within like three weeks. But I respect people who do that too because we need all voices, all ends of the spectrum. I'm also not someone who can go out and shop luxury fashion all the time, so I'm very discerning about what I buy, how much I spend, and where I buy it from. It’s all valid. It’s all relevant.

Especially working my day job too. I see people come in who are just so excited to shop, to be in person, to try clothes on—and I want to keep giving that to people. There’s something really valid about buying things and wearing things that make us feel good.

Maureen: Yeah, that word "discernment" always comes to my mind. What is discernment to you? What does that entail? What does it feel like?

Jennifer: I hate the expression "if it’s not a hell yes, it’s a hell no," but I do think there’s something to it. I feel strongly about sleeping on things, giving them a minute, feeling good about them. Trying it on. Trying it on again. Trying it on with different outfits. Thinking about what you actually need. And also—falling in love with stuff. It can be anything. Like my black boyfriend sweater from the Gap. I fell in love instantly and was like, “Hell yes, I need this in my closet,” even though I already have multiple black sweaters.

That’s discernment too. As is buying a jacket, putting it away, and three weeks later being like, “You know what? I don’t need this. No thank you.” It can take lots of different forms. The more we know about where our clothes come from—where they’re made, who’s making them, what purpose they serve, how they fit, what materials work with our bodies and our lifestyles—the more we can feel good in what we wear and develop a personal style that actually works for us, whatever that means.

Maureen: Talking about the momming of it all—are there any specific ways your style has changed since becoming a parent?

Jennifer: Yes, definitely. I'm very attuned to fabrications and materials these days because everything needs to be washable. If I can't throw it in our combo washer-dryer, it's never going to work for me. That’s a huge part of it. Fit has been a constant battle over the last couple of years. I think a lot of women—just from life, not even necessarily parenthood—experience changes in their body, lifestyle, how they look and feel, and what they weigh. That definitely rings true when you have a kid.

When I was pregnant, I wore the same black dress every single day because I was pregnant in the middle of summer in New York City. It was like 100 degrees all the time. Nothing felt good. I felt miserable. I had no sense of style—literally none. I was like, black dress, Birkenstocks, call it a day. So I was excited to get back into feeling like myself again after the baby came, but when I went to put on all of my clothes, nothing felt good. It was a lesson in: okay, what do I actually want now?

Two years later, I’m still figuring it out. There are things I would’ve loved in a past life that I put on now and they just don’t work. I’ve been in a huge closet purge lately. I’ve been holding on to things hoping they’ll feel like me again—and they just don’t. Objectively, my closet is still jeans, sweaters, button-downs, and t-shirts—nothing crazy—but the way they fit is different. I’m into more oversized things now. My body shape has changed. I’m playing with proportions differently.

We all go through that at different times. I’ve struggled with it because I tell myself I don’t need a whole new wardrobe, I have all these beautiful clothes, so why am I spending more? But at the end of the day, I have stuff I haven’t reached for in two years. It doesn’t feel like me anymore. We need to give ourselves permission to lean into our changing bodies, personalities, lifestyles, and priorities. If you see me in New York, I’m probably wearing the same five things every day. One day I’ll get more playful again. But for now, it’s practicality all the way.

In my past life, I used to work in luxury fashion and wear five-inch stilettos every day. That is just not it for me anymore. It’s rare to find me in anything other than sneakers.

Maureen: Real question: did you wear stilettos on the subway, or was it a change-when-you-get-there kind of thing?

Jennifer: When I was much younger, when I first started in the industry, I wore them on the subway all the time. Yeah. I was that girl.

Maureen: I love that for you. I just can't even imagine—that feels like a lifetime ago, when everyone was wearing high heels all the time. I remember in college, I had to wear a shoe with a heel just to go to class. What?

Jennifer: A whole different world. I'm so grateful the culture has changed. I'm grateful I work in an office where it's casual—I can wear jeans and sneakers and no one bats an eye. For that, I’m super happy. We’ve become a lot more casual. COVID obviously had something to do with it, so I guess we can put that one in the win column.

I wore heeled boots the other day for a work event. I felt great. Loved them. Ended up walking almost 12,000 steps and realized—I haven’t done this since I was 22. And I remembered why the next day. So I’m like, okay, sneakers it is for the next three weeks. But it’s also fun to get dressed up sometimes. Don’t get me wrong—I love putting on fancy shoes and a dress on occasion and busting out of my denim every now and then.

Maureen: My heeled boots have insoles.

Jennifer: Yes, wise girl. That's so wise. I should have done that.

Maureen: I have this theory and I want to hear your thoughts on it. So again, not a parent, but I follow a lot of moms on here. One thing I think we don't always consider is the passage of time between getting pregnant and then having the child—or however someone becomes a parent. There's a whole period of time where getting dressed becomes more complicated or less of a priority. And in that time, culture and fashion and everything else continues to move forward. So my theory is that when people start to feel more like themselves again after that initial period—which is not to say postpartum doesn’t last longer; I believe it lasts seven years or more—it’s like the fashion world has moved on. And when they try to go back to their old clothes, it’s not just their body that’s changed. Culture has, too. What do you think? Do I sound crazy?

Jennifer: You don’t sound crazy. It’s totally true. For those nine months or so, you kind of sit out all of the trends or the usual wardrobe turnover that happens in a year. You're not there for it. You're not shifting with a new job or season or cultural moment. Then when you come back to it, you’re like, “Wait, this feels dated,” even though it’s only been nine or ten months—which can feel like forever.

It’s strange because for me, my closet wasn’t super trendy to begin with. That was never my vibe. But even then, I went back to this pink striped button-down I bought before the baby, and it just didn’t feel like me anymore. There was nothing trendy about it—it’s just a classic oversized poplin shirt—but I couldn’t bring myself to wear it or get rid of it. It’s such a period of transformation, and everything else continues moving forward without you. I don’t think I realized how big of a shift it would be. I was that naive pre-baby person who said, “I’m never going to change once the baby comes. I’ll still be my old self.” But we’re all that mom. You can’t go through something so life-altering and not change, and that includes what you wear and what you feel good in.

Maureen: I'd like to hear more about what it feels like in your body when you put on clothes. I'm trying to make tangible something that can feel hard to explain, which is that feeling of alignment or misalignment in our clothes. Could you talk about that, maybe using the Gap sweater as an example? What does it feel like in your body to know that something is right—even when your brain says, “You already own black sweaters”?

Jennifer: I actually think that feeling stems a lot from not looking in a mirror. When I first put it on, I looked down, moved around in it, adjusted the sleeves and collar, and thought, “This is good,” even before looking in the mirror. If the sleeves hit just right, the hem is loose enough, the material feels good on my skin—if all those boxes are checked—then I look in the mirror and it’s a bonus that it looks cute.

I actually think that feeling stems a lot from not looking in a mirror. When I first put it on, I looked down, moved around in it, adjusted the sleeves and collar, and thought, “This is good,” even before looking in the mirror. If the sleeves hit just right, the hem is loose enough, the material feels good on my skin—if all those boxes are checked—then I look in the mirror and it’s a bonus that it looks cute.

For me, that feeling is even more relevant with jeans. If they don’t immediately feel good at the waist or around my thighs, or if the length is off—I'm 5'7", so I often have fit issues—then even if they look great in the mirror, it's still a no. Materials are huge for me too. I spent years wearing 100% wool sweaters that were so itchy and uncomfortable because they were cool and everyone wore them. But now I’m like, never again. Who was that for? It certainly wasn’t for me. So the test is always: how do I feel before I even look in the mirror?

Maureen: Great examples. Thank you. Thanks for going there with me. I know it can feel vulnerable to talk about how clothes feel in our bodies, especially since that’s not how we’re used to hearing people talk about fashion.

Jennifer: Anytime.

Maureen: We’re coming to the end. I'd love to finish up with what’s exciting you in fashion right now.

Jennifer: I think the most exciting thing right now is that anything goes. There’s no one way to dress, shop, look good, or feel good. That’s really exciting to me. I’m a kid of the ’90s, when there was basically one way to dress, so it’s thrilling that we’ve moved beyond that.

Personally, I love that wide-leg jeans, oversized tops, and sneakers are in. That’s what I want to wear all the time. And now there are so many ways to wear those things without looking frumpy or undone. More broadly, I think it's exciting that we’re talking more about what dressing means, how clothes impact our lives, and what fashion and style actually are. Working in fashion professionally, it's been amazing to see these conversations spill out into non-industry spaces.

Maureen: Yes, and going full circle back to your role as a buyer—introducing customers to things they didn’t know they wanted—I think that happened for a lot of people with oversized fits and wide-leg pants. At first, we were like, “Why would I do that? I’ve spent my whole life trying to make my body look smaller.” But then we tried it and realized, “Oh my god, I’m so comfortable.” That’s why I’m pro-trends to some degree. They introduce us to things we didn’t know we wanted but that improve our lives.

Jennifer: Totally.

Maureen: I appreciate your example of being excited about what we're wearing now and how many options we have. I hope it continues to be that way.

Jennifer: Yeah, I agree.

Maureen: Thank you so much. This was exactly as insightful and enjoyable as I hoped it would be, which is always lovely. Where can listeners find you?

Jennifer: I’m on Substack—my newsletter is called mom friend. You can also find me on Instagram at @jennifersandra. That’s it. I'm not on TikTok, not doing that whole game. So find me there—I’d love to connect.

Maureen: I’ll include links in the show notes.

Jennifer: Amazing.

Maureen: Thank you again. This was a delight.

Jennifer: Thanks, Maureen. So good to meet you finally.

Maureen: Likewise.

Jennifer: Take care.

Outro

Thank you to our guest, Jennifer Cook, for joining us today.

Intuitive Style is produced, edited and hosted by me, Maureen Welton. Our theme music is by Noir et Blanc Vie.

In case you missed it, Intuitive Style, the podcast, is an offshoot of Intuitive Style, the Substack newsletter. Head on over to Substack, search Intuitive Style, to see the newsletter, which includes thoughtful reflections on what’s happening in the fashion world, guest features, and my encouragement that you can create a wardrobe that fits your life as it is now, no judgement, no rush.

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