

23 Mar 2026 · 46m · 16 chapters

In this episode, Liv Perez and Larissa Mills discuss the resurgence of interest in Carolyn Bessette-Kennedy (CBK) and dissect what truly made her style iconic beyond just the clothing. They explore the misconceptions surrounding copying CBK's style and delve into the essence of personal style in the modern context, especially in the age of social media.
Written by AI. May contain mistakes.
Discussion on Carolyn Bessette-Kennedy's style and its misinterpretations.
“Let's go get dressed with Larissa Mills.”
Hosts reminisce about the fashion trends during CBK's era in New York.
“So I want to set the scene a little bit because you lived in New York during this era.”
Exploration of CBK's unique aura and her approach to personal style.
“now obsessed with like, you know, any Hollywood couple.”
Analysis of the relationship dynamics between Carolyn and John F. Kennedy Jr.
“It was like, it was like you had like the Ralph Lauren, world over here and you have the CK world over here.”
Explore how Carolyn's style is being reinterpreted and its cultural significance.
“you know, I feel like on Instagram, we're seeing like, you know, if you get this exact coat, you're going to look like CBK.”
Learn how to engage with fashion trends while maintaining personal style.
“And so it's kind of, there's a novelty around that, but yeah, I think that's, it's, you know, it's very marketable.”
Understand the emotional aspects of clothing choices and their impact on self-perception.
“So I feel like that's part of the, that's part of it to process.”
Delve into the importance of dressing for oneself rather than societal expectations.
“I think about this all the time, which is that— Good.”
Explore how hair influences personal style and perception.
“her silhouette as you and I said, like she wears kind of like the long, everything's a bit longer.”
Learn about the significance of proportions and silhouettes in dressing.
“like in, you know, cause the, like a beaded bag or something, you know, the whatever.”
Discuss the balance between dressing for body type and personal style choices.
“So I should be wearing something that's a bit more low slung.”
Discover the concept of minimalism and editing in personal style via CBK.
“I was going to say, mid-range isn't going to work.”
Understand how repetition can lead to a strong personal style identity.
“And this is where something is not, like to me, there's a little bit of a disconnect.”
Get tips on choosing appropriate attire for a mother of the bride.
“And that was just being cycled in different color ways.”
Learn how to maintain your personal style while dressing for weddings and formal events.
“of black even, but if it's a black tie wedding and that's what they want and that's the look of it, then it can be fabulous.”
Discover tips for bridal styling, including recommendations for dresses and fashion accounts.
“Like you don't need to undersell yourself either.”

Get the gist, explore an idea or ask about something said.
On Let's Get Dressed, what are the key points of this episode?
Automatic transcript. May contain errors.
0:02Hi, everyone. It's Luke Perez. Welcome back to another episode of Let's Get Dressed. Today, we are diving in to all things Carolyn Bessette-Kennedy. I feel like it was time we had this conversation on the podcast, but we are mixing things up a little bit because I invited my friend and fellow content creator Larissa Mills onto the podcast after she wrote a very compelling story for Marie Claire about how everyone is getting CBK's style wrong. She lived in New York during the CBK era and is also a lover of fashion. So I think we could learn a thing or two from Larissa on the matter. I loved having this conversation with her.
0:35We talked about a few of the CBK tools, what she used to further define her style, what really even is personal style today, and if she really had good style or just a really strong aura. I hope you guys love this episode. If you have time, please leave us a review on Apple Podcasts and Spotify, and make sure you follow Larissa on Instagram as well. Let's go get dressed with Larissa Mills. So today we are talking all things Carolyn Bissett-Kennedy, CBK. And I feel like it was time that we had this conversation on the podcast as a fashion podcast with so many things on social media and just in the world going on.
1:09If you guys haven't watched the show yet, the show called Love Story, which is on FX and Hulu right now, it tells the love story of Carolyn Bissett-Kennedy and John F. Kennedy Jr., which has been a fun watch. Have you been watching? Oh, yeah. I didn't want to, honestly. I was like, no, I'm not watching it. But then I had to. Everyone's like, it's an enjoyable watch. Regardless, it's an enjoyable. I'm trying to like disconnect the two strains of thoughts in my brain. Like I'm watching it as like a guilty pleasure, but I'm not taking it as real life. And like I'm disconnecting a little bit. Yeah.
1:39Yes. It's been a fun watch. But what I think I've been most interested in analyzing is this kind of like frenzy online about, you know, how to look like CBK. Like get these boots and this skirt and these sunglasses and you'll look like her. So I really wanted to put some content out there that serves as a little bit of an antidote to that and kind of break that down as well for, you know, this show that talks about personal style and like what that means every week. And it's funny as I was ruminating on this and thinking about it and look like I just also want to make it clear like neither of us are coming from a place of judgment.
2:12I think a lot of people are meeting CBK for the first time and are really excited about her personal style and like what that means. But you wrote an amazing story for Marie Claire about what people are getting wrong about copying her personal style. And I thought it was great. So I was really excited to invite you on the show today and talk about it a little bit for a few reasons. One, you lived in New York during the era, which I cannot wait to hear more about. But you also have like what I like to say is like impenetrable personal style. Like nothing is ever knocking you off kilter, like I can see something and say that is Larissa.
2:51And so I'm excited to talk today a little bit about what the experience was like, but also for people like who are interested in looking like her and dressing like her and shopping, like the more anti-internet CBK way to do it from the both of us. So we'll get into that a little later in the episode as well. So I want to set the scene a little bit because you lived in New York during this era. So tell me what were women wearing in New York during the CBK era? Well, I think that's the thing. And I'm not the only one that's noticed this because a lot of the women of my age group, it's kind of, it's been sort of a hilarious side chat.
3:27It's been on all of our phones where we're all like, I mean, everybody dressed like that. It was sort of like the frenzy that was happening was a little bit like, okay, like the stuff. Yes. Like she had, she had great style, but it really was the uniform. There was definitely that, that, that uniform of the nineties. And I think I wrote, I did two different pieces, but like I was shopping at Banana Republic at the time and, you know, she was wearing Prada, but it was a very similar, it was a similar silhouette. It was minimalism. It was, it just was sort of a sign of the time. So everyone kind of had that mood.
4:05I, so we, we were all kind of, not that we wouldn't be shocked because she definitely was making waves just how she carried herself. I think that's what it was at the time. To be honest, I remember always thinking that John had the amazing personal style. Hopefully people won't come at me, but like I always felt like she looked great and of the moment, but I never fully was thinking like, oh my God, I've never seen anything like this. I think it was really more about her. So it was the combination of the two of them and her. Yeah. I could imagine that John's style felt more avant-garde for the time than hers did.
4:46I mean, we're talking about the nineties, like Calvin Klein was the biggest brand in the U S for sure. Every woman wanted to dress like the Calvin Klein woman. So it begs the question for me, like, was she a style icon in that moment or was it more about like their relationship? Like were people obsessed with them the way people are now obsessed with like, you know, any Hollywood couple. I think so. Although I, and I, I, I say that, you know, trying to think back, like, I think really the, the real thing for me, where I will say her wedding dress, that I feel like that was something where she was doing something different than what other people were doing.
5:23So like when now I'm looking back and going like, okay, like there was that, that, that, that, but where I personally felt like, oh, wow. Like I'm gonna like take note of her personal style it was her decision to wear that dress because up until that point I feel like a lot of the dresses like now it would I feel like it's no big deal probably a slip dress but it was so pared back it was so minimalist it was it looked very new different interesting fresh so for that like so she she probably did it's just that I none of me all were sort of I worked actually it was interesting I worked for a hot minute for Ralph Lauren and like my coworker was working for Calvin Klein.
6:04It's all during the time. So that's where it was sort of like, well, yeah, like that's what everyone wants to, it's that kind of look. But it's, it was the wedding dress where I think I really was like, okay, wait, she's got, she's got a very specific point of view. Like she's not just wearing the clothes. She actually is of this. There's something of her that's, that's part of the magic is really what I'm I'm very rad about. You worked at Ralph Lauren in the nineties. Okay. Literally like managing, like, like, like this was, this was, I was not working as the PR person. I'm the 22 year old at Saks Fifth Avenue, like in the managing the, they had like, oh my God, it's so different now.
6:45It's like the fifth floor. And we had like CK, we had Ralph Lauren, we had like, they had these little, like almost like built-in boutique type. Like a stop and shop. Like a, yeah. It was like, it was like you had like the Ralph Lauren, world over here and you have the CK world over here. And it's just kind of funny because at the time I was like, I'm going to get, I'm going to get over to the CK world because CK felt so just very cool, obviously at that point in time. Do you ever see her in person? I saw her once. I saw John all the time. And again, maybe that's part of the, it's just, he was constant.
7:19I think he wanted to be seen more way more than she did, to be honest. So, but I worked in advertising and I don't even remember where his offices were, but they must've been close enough that I would see him, the bike, the whole thing. But it was just, he, he just to me had like, it was the accessory, accessorizing that he did that always, that I always sort of noticed. And which is not something that like most of the guys that I knew were wearing, whether it was advertising finance, like they just didn't, he definitely had a, had a cool look. And now apparently guys are copying him now too. So, you know, it's funny.
7:53I actually saw a video of someone, someone posted on Instagram, like a guy crossing the street in New York and he was wearing like a backwards hat, but I feel like men in New York dress that way anyways. I think they do. I agree. Yes. Like, I don't think that this is a new thing. Like this is like the way I feel like New York men have always been like that vibe is, is there. I agree. I think it would be, I think it would be more shocking if I saw like men in suits all day in New York. That's actually a good point for you, for you right now. Yeah. I'd be more shocked by that. For me in the, in the nineties, like people, that was like, there was a uniform and like, he was not, he did not, he wore it differently.
8:32Like he kind of made things casual. He had the different hats. He just, even the riding the bike everywhere. That's not guys. I knew like they, if you're close enough, they were walking, they were taking the train. Like they weren't riding a bike everywhere. Do you think for her it's more about aura? Like, do you think that there's like a way that she carried herself differently out in the world? Like having seen her that one time that like feels different. Totally. Cause it's funny that even when I saw her, it was from like probably a block away. And it was one of those things where you kind of go, wait, I mean, obviously she's on like new, you know, magazine covers, whatever, but it's still, it's one of those ones, a certain type of person aura is around you, you kind of, it's like an instinctual that you are drawn to it.
9:20So I just, I think that's really what we're drawn to with her. And I think that's true with a lot of people that get elevated, to be honest. I mean, but I think my whole point was that she just seemed, my big thing, my big thing is, is she wore the clothes, right? You could tell that it was not, it wasn't a costume or a uniform or like, oh, I'm wearing what's current. It's really was like, there was something about her that it just felt like it was very intentional. Yeah. I think about what that would look like today. Like, would it be as impactful today? And every time I think about that, I think about just the change and like what we have access to from like the 90s to now.
10:07Like I open up my Instagram and I see hundreds of incredible women with unbelievable style. And I wonder, truly, in watching the show, I've been like, would this be as impactful today? Or would it just be about their star power? I think so. Okay, a quick break from today's episode to share my Depop find of the month. Since we are talking about fashion, I had to share this one. Today's segment is brought to you by Depop, which is one of my favorite places to shop, especially when I'm looking for something special. This month, I found this incredible Dries Van Noten stripe button down. I love this top because it has that like slightly unexpected Dries stripe and colorway.
10:50The proportions are really relaxed but tailored. And those are the pieces that I immediately want to add to my wardrobe because they make everything look so much cooler. And you guys know for the podcast, I'm always looking for really great tops, things that stand out through video and feel really exciting and like my personal style. And this feels like a perfect addition to that. It's classic, but a little bit offbeat, which I feel like is a Dries Van Noten staple. I love all of their pieces so much, and I'm so glad I found it on Depop. Lately, I've actually become quite picky about what I want to bring into my closet.
11:22I want to make sure that it could be worn in a lot of different ways. Like, can it be worn with jeans? Can it be worn with cool pants over a skirt? Can I dress it up? Can I dress it down? Is it interesting? Of course, we all love our wardrobe basics, but I find that it's like the exciting pieces like this that really are the foundation of my wardrobe because they feel special and feel like my personal style. I have a trick for going through Depop and finding those pieces for you. And that is using keywords. Don't just go on Depop and doom scroll. You will be there for hours. I always say when you're searching, search with intention.
11:53So I went on there and searched for Dries Van Noten Top and searched from there. It's also so easy to refine from there through price point, fabric, etc. So you'll be able to find something that truly suits you. And bonus, if I find one good piece from a seller, I'll usually click into their full shop and that's where I'll really find the magic and I'll save them to my profile so I can always go back. I feel like it's about finding the people out there that have similar style to you and connecting with them because at the end of the day, those are the pieces that are going to resonate the most with your personal style and also how you're going to meet amazing other people who love fashion too.
12:24It's almost like discovering a mini boutique through somebody else's point of view. And that is my favorite part of Depop. And if you're someone who has a strong point of view through your personal style as well, someone out there probably wants to share it as well. Even if you're someone who's cleaning out your closet right now, a lot of people turn to Depop to list their items because you can literally list in minutes. Their AI-powered listing makes it so easy and fast. There's really not a lot of work that needs to be done. They do item descriptions, smart price recommendations, and key details that are populated automatically for you, which make the whole process seamless and totally worth it to see somebody buy pieces who will really value them as much as you did.
13:01Best part, there are no seller fees on Depop, which means that you get your money directly in your pocket. You can so quickly and easily turn clothes that you're no longer loving into extra cash. Okay, a little legal disclaimer, payment processing fees and boosting fees still apply. So see the website for details. But for me, it really starts with the hunt. If you are looking for something specific, or maybe you want to discover sellers with incredible taste, Depop is such a great place to start. Download the Depop app and list your first item in just a few taps. Okay, back to the episode. Okay, quick pause from today's episode because I have to tell you guys about a few of my favorite pieces that have been on my mind this spring from one of my favorite brands, Banana Republic.
13:40Lately, I have been so intentional about what I'm adding to my wardrobe. I'm really in this phase where I care a lot more about quality, pieces that just feel worth investing in that I will actually reach for over and over again. And Banana Republic has always been my tried and true. They have always been known for their workwear, especially those iconic 90s and early 2000s campaigns, which I feel like is really trending right now. For me, getting dressed for work doesn't really look the same every day. Some days it's a 9 a.m. meeting and other days it's recordings, fittings, events. So I really need pieces that just feel put together and super easy.
14:14The archive-inspired suede jackets, like this one, feel very classic Banana Republic. It's structured, but still really relaxed. And of course, the tailoring has such a great polished look, but it's genuinely comfortable for your everyday life. It's that balance of structure and ease that I'm always looking for in my wardrobe. So for all of your spring shopping needs, shop New Arrivals at Banana Republic. I want to zoom out a little bit because, you know, I feel like on Instagram, we're seeing like, you know, if you get this exact coat, you're going to look like CBK. I think people even like, let's talk about the the resell of her exact items are going for hundreds of thousands of dollars.
14:54What is it about like now that you think people are trying to kind of reinterpret the looks like through replication? Like, do you think that lands the same? And why do you think it's resonating so much right now? It actually ties back into our first conversation with the thing that you had said, like if you could change something, what would it be? And I had said, like, I wish we could slow fashion down. Like I wish we could just slow all of it down. And back in the nineties, it was way slower. Like you didn't have, like you're saying, there's so much out there. There's so much to choose from.
15:27There's so much content. It's just, I kind of think that what is going on now. And it's like the good and the bad, there are too many, there, there are so many choices. There's so much noise. I mean, I can't even go on Instagram now. Like I just, I'd never go on TikTok. I'm, I don't scroll. Like it's just too, it's too much. It's definitely taking you out of, it's like, if you do yoga or any of that type of mindful, I'm not very good at all that, but I like the, I like the, I like the idea around it, but of being in the present. And there is something about scrolling and all these things that is most definitely not in the present.
16:02It's just like, it's a, it's like a, it's like an ADD, like, oh, that wait, I have to be over there. I have to be over there. It's a constant, but I think, I think what's going on a little bit with her and where it's like, it's honestly, it's not their fault. There's so much information. There's so many different styles. There's so much going on that it's really appealing to, which is why the whole, like this aesthetic, that aesthetic, everything has to like, they're trying to break it down. And I realized I was like, they're putting labels and trying to categorize because it's impossible to deal with this much information coming at you.
16:40You, your brain, I think at this point, like there has to be some way to organize this. And so that's why you have like tomato girl and what all the different cottage core and whatever is they're trying to like figure out different categories to figure out where do I fit in? There are too many choices at this point. So like, I think with Carolyn, it's a very easy, it's very easy to sort of, oh, great. Like this is, we can call, we can replicate this quite easily. We can like, this is doable. This is in a way it's attainable. And it kind of takes away the stress and the anxiety around, you could be that girl, that girl, this girl, this girl, like, who do you want to be?
17:24I don't know. I think that may be part of it. It's like they say with child raising, like you don't say, what do you want for dinner? It's like, you can have, you can have chicken or you can have fish. Like we're narrowing this down for you. And I think, I think that's maybe part of it. And obviously you have a TV show that is on, it's nostalgic, the nineties where some of us are reliving. Some of us are finding it for the first time. Like you're saying, like it's getting, people are being introduced to her. And so it's kind of, there's a novelty around that, but yeah, I think that's, it's, you know, it's very marketable.
17:59Very marketable. But I am curious from your end, like while we're talking about just like kind of all these like micro trends, which is what I like to call them. You're someone who's in fashion and you're constantly inundated with trends. How do you engage with them in a way that you feel is like healthy for your personal style? Well, it's funny because back to the like, I'm not consuming much. So a part of me, it's weird. It's like I try to get the trends through. I don't even know how to explain this, like through osmosis of like being around in the city or somewhere traveling, but I don't like, I don't study it.
18:32I couldn't tell you if you showed me a bunch of different outfits, I, I'd probably have like a low average of which one was which designer. Like I'm not studying it like that. So I try to sort of breathe in what's happening generally and form it into my own style, as opposed to like really being on top of it. if that makes sense. Like I, whatever, like, it's almost like my own natural filter. So I don't, I'm just not part of it too. I don't want to be, I don't like being online so much that I don't want to be influenced. Like I want to have some separation where I can feel like I'm coming into something on my own because it's a natural evolution that things do kind of come around.
19:19It's just like, I don't know, certain looks, they start to feel fresh again because you haven't seen them in 30 years or whatever. And so that's just like a natural thing that we all are kind of going through it at the same time. But if I see stuff too much, then I'm going to feel like, Oh God, am I copying that? Or am I just naturally gravitating? And I don't want to just copy. So I don't even know if that answers the question, but it's like, I, yeah, I don't, I don't pay attention a lot. So I feel like that's part of the, that's part of it to process. Yeah. it's because I don't actually see a lot.
19:54So that's a good thing. Like I'm able to not, I'm not overwhelmed because I'm not looking at it. In your article, you said that her style was a really good lesson in discernment. Can you break that down a little bit and what that means and why you think it resonated so much with you? I just think that like she had the, she had, she had way more choices than most of us had in terms of a wardrobe. And she obviously could have worn, you know many different things could have whatever she you know even jewelry she was very minimal in her jewelry choices she was so her makeup I mean again like this is a woman who she could have put she could have had makeup artists she could have but she clearly like made a very definitive choice to to keep things very pulled back and under understated and it seemed like it was part of her overall personality too.
20:47Like it fit with her personality. That's another part. It's just like, if you're this part, like life of the party, and then you're trying to pause play CBK, like, I don't know. It's not a fit, you know? So everything's sort of like fit to who she appeared or seemed to be from not knowing her, but it resonated. Like everything was resonating on, on all levels. Like good for her. I don't think she wore mascara and that's just not going to happen for me, but like she did it. And she, and again, it's just like, I could never, I don't think the no mascara, like I love mascara, but I love that she kind of went there.
21:25I don't know. It's just like, there's a confidence in her style choices. I'm currently working on this myself is like, how do you go into a wardrobe full of clothes and decide what's for you and what's not for you? We all buy things sometimes on impulse. Maybe there's like some things in our closet that we never wear, but we just like kind of keep them there. How do you think that we can take that same level of discernment into the way we get dressed every day? There's a bit of Sybil, which is why I like Carrie in a way, because it's just like, depending on the day, like sometimes I feel like I'm so, I'm, I'm lazy.
22:03I don't want anything to be tight. I want it all loose. I'm almost slothy, slobby girl. And then other times I feel like I'm very like things are structured. They're tight because I'm in the mood for that, but I wasn't in the mood for it yesterday. And that's okay. I think the, the third line is just like, there might be probably colors I'm drawn to, or I like layering. I like pattern. I like, you know, I like something that's going to like, I don't know, be unexpected. No, I've had many, many, many mishaps, but I look back and I'm like, well, how would I ever wear that? But like it fit the mood in the day, you know?
22:42I think a lot of times though, it's like, what do I feel? Like I feel such a, I don't want to say good wearing. It's not about feeling good. It's, I've often felt like, it depends. It's like how I want to move through the room. It depends on the environment. Like if I'm in an environment where I'm going to be sitting at a very, like, it's more formal, I'm going to be standing most of the night, there are certain clothes that are going to resonate with me than others. If I'm going to be around like kids and like, it's more informal, I want to move. There's a way I'm going to move through that room that I'm, that will be different than others.
23:18There's also sort of like a protection that clothes have for me. So if I'm in a situation where I feel more nervous, which is most of the time in any like social situation because I'm, I'm more introverted. So being out in that, a crowd or whatever, I tend to have, it's almost like an armor. Like there are certain pieces that I feel like I have like a little bit of space or like protection. It's weird, but yeah, like some clothes are more vulnerable than others. So it's, it's got a lot of emotional clothing. Clothing has a lot of emotional components to it. I think. I think about this all the time, which is that— Good.
23:57Do I go outside sometimes and pick an outfit based on the way that I want the setting that I'm going into to perceive me? Yeah, yeah, yeah. Absolutely. Which I think is not good. Like, I think everybody does this. Yes. Do I necessarily think it's the healthiest thing ever? Absolutely not. But do we all do it because we're human? Okay, but explain, explain, explain. Go further with that, to me. I would love to get to a point where I would love to wake up every day and dress for my eyes only and what makes me feel really good and not wear this like very fashion-y dress to— Okay, I get what you're saying now.
24:33I get what you're saying. A dinner where someone's going to be like, whoa. You know, like I sometimes will dress based on the room that I'm walking into. I think we all do that, but I want to get dressed for myself every day and not for the things for perception. I see. I see what you're saying. Okay. There may be a point to like, as you get older, there is a little bit of, you're not, it is easier. I have to say when you're older, I feel like it is easier. It's easier. It is like, you just don't care. You can't even take credit because it's really just age does it. So it's not like time has been the most beautiful gift for my personal style.
25:09Time is the true unlock. And like I'm only 32, but like looking at who I was 22 to now, I'm like, oh my God, those are different fashion people. And thank God what a gift time has given me. I would say though, okay, turn it around when you see, cause this is how I feel when I'm in a room, when I see everyone, I'm like, yep, I actually, I just, I just wrote something today about bags. And my point was there are like it bags. I'm like naming things now. There are it bags, which we know. And I named, but there are now bags. Stay with me. So an it bag is like what we all know is the it bag because they told us it's the it bag.
25:48And then a now bag is basically like, it is very, it feels very of the moment, feels very current, but like I've chosen that now bag because I can see there's something in it that is resonating with the times, but it is not one of those bags. Okay. So to me, when I see a woman at a, let's say a party. And I see a lot of them that I'm like, yep, yep. Check, check, check, check, check. Right. They've all, they've, they've checked the boxes, but then there's one person that is like, huh, that's not quite, that's always the one I'm going to look at. That's always the one that I'm always sort of like, Oh, like she's, she's got something going, like she was confident enough to break out of that and kind of do it in her own way.
26:36And so I don't know. Like, I feel like at the end of the day, I find that I'm more intrigued by that, that one that's, I guess they're more vulnerable and they are, it is a more vulnerable, but that's where like that there's like a confidence that comes in with that. So, and I mean, you've, you have earned that place to dress for you, like just for you. So yeah. I mean, you have, you, you have all the knowledge of all the designers and all the, and to be able to, you have all that foundation behind you. I feel like now, like you just, you just need to go with just, just you. Yeah. I went to, I went to dinner on Saturday night and I was wearing the new Chanel shoes with the, they're like square toe.
27:19And a guy was like, I hate those toes. And I looked at him and I was like, I just was like, this is not for you, buddy. This is not for you. Thank you so much. Exactly. Love your khakis. Exactly. Love your khakis so much. Oh my God. So I want to get into a little bit of what I like to call like the CBK anti-toolkit. So for people who are out there in the world, I want to share how people can like take inspiration from how she dresses and make it their own without exactly copying what she wore. And there are like a few tools that I think she has that like I really love. And one of them is like, she really knows her silhouette as you and I said, like she wears kind of like the long, everything's a bit longer.
28:06She is a bit taller. I also think hair plays a bit, really big role. Her hair is really long. Yeah. Hair is, hair is everything. The hair has been the accessory. And I mean, I have to laugh. My daughter did send me one thing that was funny. Like I'm sure I'm missing most of it, but the pen, the hair, the smoking. I'm not a smoker, but I literally, I'm like, I want to like, why is everything look cooler? And everyone's going to go mad because you're not supposed to, I'm not promoting it, but like, she looks cooler doing it. She does. I'm sorry. I think the hair stuff is, is so real. Like the hair stuff is, and I say that maybe because I'm a jealous brunette, but like, I can think of like five blondes right now who I'm like, your style is better because you are blonde like that.
28:51And the picture and the vibes, like, Yes. It works. Exactly. Carolyn Zach Kennedy is one of them because like that long blonde hair made everything just look. Yes. So it like, it adds so much to it. Does it add color? I can't pinpoint it. Well, it's like, for me, it's light reflection. I really love, I love light reflection like in, you know, cause the, like a beaded bag or something, you know, the whatever. So there's light reflection with that and there's movement and it may, it somehow it makes it, there's something effortless and carefree about it because it doesn't have like a, an uptight feel to it.
29:28There's a freedom with it. And I think that's what, again, so that would be another element, like, okay, maybe it's that I'm wanting to, I'm drawn to like light reflection and more free, free flow and casual. And okay. So like maybe your jeans are super casual. Maybe they're a little bigger and they're a little low, or, you know, you're, you're not wearing tighter, tight silhouettes, you're wearing things a little bit looser. Like maybe that's going to give you that feel. I did love her jeans. I have to say, like I liked the, I really love, I do love that slight boot on her and the shorter because I like how you can see the shoes.
30:07Like, I don't know why that is like one of the things that pulls me into her. Like I like seeing those shoes. I like seeing those shoes and those shoes and those boots, but it's partly because those jeans are cropped where they're hitting. Yep. Yeah. Let's talk about this a little bit because I think proportions are everything. And it's something I've learned a lot in the last like 10 years of getting dressed every day. I think only now at 32, I'm beginning to understand my proportions. Like I'm a low slung girl. Like I high waist cuts me so strangely. Like I should not be wearing high waist and I've been wearing high waist for 10 years.
30:39Okay. Guys, we're figuring things out in our thirties. We're really coming to, but you know, she wore things like she was tall. It made her look longer. Like I have really long legs, but a short torso. So I should be wearing something that's a bit more low slung. And I completely agree that that one little tailoring detail of being able to see a shoe can change an entire outfit. So for you, how have you been able to dress for your proportions? Okay. Well, I'm not the person to ask because proportionally, I should never wear anything low slung ever. Never should I ever do that. Except that again, moving through the room, like I, I like, I also am sort of a lazy.
31:19So I like to, I don't want to have something always like up on my waist or feeling around my waist. I like it low because that kind of feels like they're falling off. And I like that slouchiness, like a jean. I stopped dressing for my body a while ago because I was sort of like, but I like that look or whatever. So I just did it. see, I love this. Okay. No, I do. It's funny because I've never seen you wear something and been like, that doesn't work on her because you do lean into like the oversized, the layers, and it just kind of works. So I think you can be both ways, but I think Carolyn specifically really dressed for her body type.
31:56She definitely did. I mean, I would, I'll tell you, I'll point out when I, when I have a, if it's a long dress or like a long skirt, it's not great on me. And I know that, but I don't care. I still like the look, but it does some somewhat swallow me up. Like I look like a child that's wearing mom's clothes a little bit. So how do you offset that if you love it and you feel like it doesn't work for you? I don't care. I don't know. I don't care. Like I just am like, I don't care. I like the long skirt, whatever. It's not the best. Yes, it shortens me, but oh well, like it's... But I love the skirt.
32:27But I love the skirt. So see, crazy eyes for the skirt and I'm going to wear it. Even today, I'm wearing this skirt that's like high-waisted and I don't really think it's my best, but I love this skirt, guys. See, you can go. Exactly. You know what? Bravo. There you go. What am I supposed to do? Take it to the tailor and like get it taken down to my belly button. I mean, I mean, I sometimes I'll like, okay, the long skirt, like I probably will, will, I'm not even doing a purpose, but maybe I will wear a high, like I need, I feel like I need a heel. You know, it's really annoying. Look, here's what I'm just annoyed by in life in general.
33:02Yes. Everything I wear looks a hundred times better with a heel. It really kind of does. And I... Yes, agreed. You know, it's one of my only benefits of living in LA is that I can wear my heel and get in the car. But I have an entire wardrobe of heels. And it's like, girl, where are you going? Like, I don't know where she's going. Wherever you want to go. I know, but I have been thinking a lot about like, you know, one of my hardest, and this is so dramatic, hardest fashion questions is when I'm at the tailor and she's tailoring my pants. And she's like, do you want these for heels or for flats?
33:35And I'm like, one time I said, do it for both. And she looked at me. She was like, that's not a thing. And I was like, let's make it a thing. Give me a mid-range. But I did do that with one pair of pants once and now they just look funny. Exactly. I was going to say, mid-range isn't going to work. Nope. For either. So now you're just, it's an either. I think this is like really refreshing. I think a lot of people are like, follow the rules, dress for what's best for you, make you look your best. But like, there are pieces that we love and we're going to - They are. I'm just doing it. It's also like the reality also is like, it's very expensive to have a very tailored wardrobe.
34:09You have to either be model size, which is no one on this planet, or you're taking every piece to the tailor and getting it perfectly fit for you. And that's just not realistic. And that's okay. I mean, I'll cut pants. I used to do this in college. Well, I'm still there. Yeah, I used to literally take scissors to things and like walk out the house with a raw hem because I was like, they didn't fit. No, you know what? They didn't fit. I like it. It's also a look. A raw hem is a look. It works. And for me, trust me, there's still like I'm cutting. I mean, you're cutting a huge amount. Yeah, it's a huge amount.
34:40And I'm still keeping it really long. So you're not you're barely even seeing it anyway. So right. Right. Okay, guys, you heard it here first. Either way goes just wear what you love. Yeah. Okay. My second tool that I've learned from CBK is and one thing that you said to in the article is that she edited ruthlessly. So what does that mean? What do you mean when you're talking about editing your wardrobe? Does that mean, does this go back to the discernment conversation? Fill us in. Well, I mean, the thing is like, I don't actually know if she did that. I'm, that's what it looks like. Right. Okay.
35:14Right. Like everything in this episode is speculative guys. Everything in this episode. But like, it just seems like she had a point of view, like she had a fashion point of view and she stuck with it. So like, to me, like obviously color palette, like she did not stray. It seemed, although I did see a picture of her in some like floral pink skirt and I, and I nearly like fell over and to be honest, I didn't love it. Yeah. And I didn't love it. I, that was the one time I remember I saw a picture recently. I was like, that just doesn't to me, not her. Like, did somebody else dress her? I'm confused what's going on.
35:49So that aside, like it just seemed like she very much gravitated toward the neutrals, the, and she stuck with it and everything was just minimal. But this is why I mentioned the makeup is because you'll see someone putting on the minimal or quiet luxury look and they have a full face of makeup. And this is where something is not, like to me, there's a little bit of a disconnect. Like someone in this true quiet luxury, quiet luxury to me is that what she was leaning into, this Kennedy world, this no makeup, hair down, chic East coast thing. And it was very much, I mean, especially back then, very much a look and a thing like girls, women in that circle, they didn't wear makeup at all.
36:43It's just like, there were certain markers of this world that I feel like she embodied too. And I don't know, like, was that on purpose? Like maybe she was leaning into this world. You know what I'm saying? Yeah. When I think about her style, the first thing that comes to mind, if I was like going through her closet right now, it would be great jeans, a bunch of simple white tees and black tees and an unbelievable jacket and coat closet. Yep. That's it. Bag. A great, great bag that she wears all the time. Right. It's very well made. But she repeated those things a lot. And that was like another tool I took.
37:20Again, like I looked through her style and I was like, what are these like tools that we can learn from her. And like another one was that repetition that you and I were talking about earlier. Yeah. I think the repetition is one of the key things that because she's, she's really saying like, she's short of her choices. She's not all over the place. So to me, that's where I go. Okay. Yeah. Like I can wear the same pair of jeans over and over and over. That's fine. Like there's no reason to mix it up for the sake of mixing it up. You know, it works, wear it. It's funny. This exact thing that we're talking about is the antidote.
37:52to modern day personal style on the internet. Because think about it, on the internet, we're just told all the time, newness, buy this new thing, try this new trend. But at the end of the day, is what makes someone have the most recognizable personal style is repetition? Yes. I think it is. Yes. Because I think about, let's even, let's go back to like Haley Bieber in like, you know, 2016 era, right? Like I can recall very specific things that she wore on repeat. It was the Bottegas, the Bottega in Trechato sandals and the bag. And she always had a great leather jacket and glasses. And that was just being cycled in different color ways.
38:34And it was the moment that defined her as a style icon. Yes, think about some of the designers like Karl Ockerfeld, who wore the exact same thing over and over again. and it became like, oh, that's iconic. Why? Why? Because he made it so because he was so sure of it. He asserted, this is my look. I mean, it's similar. Like I feel that way about like someone who always wears lipstick. It's kind of like a signature fragrance. If you establish that, then it works. And she definitely did that. I agree. What gets repeated the most in your closet? I mean, jeans. Jeans. Yes. But you also like this morning, I was thinking about you.
39:09I just want to see your skirts section. Oh, I love skirts. So do I. I love a skirt, but you really, to me, when I think of you, the first thing that comes to mind is like the power skirt. I love a power skirt. I love all skirts. It's the silhouette. I think that's actually more the, like, and to me, that's how you, instead of trends to me, and I don't know if we talked about this, but like, to me, it's not about like the exact pieces. It's really like the silhouette of it. The silhouettes are what change. But if you are a vintage consignment-y type shopper, you will realize like this has been done.
39:4340 years ago, this was done. It's repeating. So like what is it? It's a silhouette change. Go look at Christian Viewer over the years. Like they all, it's all the designers have their different thing, but the silhouette they followed. It's the silhouette. So. Yeah. I mean the bar jacket, everything starts with a bar jacket for them. Yes. And the silhouettes follow from there. Okay. To close out a new series on the show that we are starting with you today. I'm very excited about it. It's called Let's Get You Dressed. And it is the answer to the trickle in of DMs that I get from people asking what to wear to certain things.
40:20So I posted on my Instagram for those of you who maybe want to get a chance to be shouted out on the pod and help me and the guests figure out what you need to wear for a certain occasion. I will always be putting a little question box on my Instagram on the weekends ahead of recording so that you can submit. But I thought one that was perfect for you. We have Debbie, who is a mom and her son is getting married. And she wants to know what to wear for her son's wedding. I checked out her Instagram. She's like so beautiful and like very classic style. They live in Massachusetts. So they're on the East Coast.
40:54Forget like a specific brand, but a website, I feel like I there for a mother of the bride moda operandi is without a doubt to me, for me, I go nuts over the formal, like what they have to offer. It is, it's so pretty. And it's like, I feel like they, they do have a little bit like different. Some of them are a little bit different there. I don't see them everywhere there. They have color. It's not just a sea of like black dresses, evening dresses. They don't, they don't look like, sorry, but they don't look like game show host. Right. Evening gowns. Yep. That's a tough one. I think for mother of the bride dresses, it's like, how do you find something that's pretty and doesn't feel like you're on a game show?
41:39I totally agree. I hate to, but like they do lean to that. Like if you go to a lot of sites, a lot of the evening wear, like when you see formal or mother of the bride. You're like, like it does not. Yeah. Any do's and don'ts. Don't wear white. I know. Don't wear white is true. I'm not a huge, again, it depends on the wedding. Like I'm not a huge fan of black even, but if it's a black tie wedding and that's what they want and that's the look of it, then it can be fabulous. So it depends. I think it depends on the woman, but like, I feel like they, they, it's kind of like prom where girls all of a sudden they never wear their hair up, but then for proms, they think, oh, it's prom.
42:19I should wear my hair up. And they do the prom hair. Please don't do that. This is so spot on. Just be, it's you, whatever your style is, whatever that is, since we don't have any parameters, whatever her lean into that, but just elevate it for this occasion. But like, don't become somebody else for this occasion. Like I don't, I also don't really, I don't love like you become the Easter bunny. Like I feel like there's like a big mother of the bride Easter bunny thing that happens. Like you have to wear some bright color. Again, if you're a color person, great. But like, if that's not you, then you, then you don't need to be Easter egg colored.
42:57I've, I've seen that a few times. Like it gets very pastel-y. It gets very pastel-y and they think it's a wedding and they think I'm going with spring. I'm just, but like, they get very pastel-y. It's like, you never wear pastels. You always are like, you're like the beige person. And now you're in like pale pink. Don't do that. I would wear pale pink. Right. But you wear a lot of color. Exactly. I wear a lot of color and I love pink and it's like not, it's not a jarring thing. So yes, I agree. I so as someone who like my wedding was in the last two years and like I had, I have four sisters and my husband has three sisters.
43:28And so we had literally 10 women to like help get ready. I completely agree. It's like, don't try to become this like alternate version of yourself. Stay in your color lanes, like do the kind of glam that you usually do just like up a little bit more. I was going to say, I really like what my mom wore to my wedding. She wore this like Monique Lillier kind of like beautiful bodice, but it had this cape that she wore for the ceremony, like a chiffon cape, which I'm not going to lie. I really do think for Mother of the Bride, there's something about a cape or I know that we're kind of over the scarf thing, but like I do think there's something very beautiful and like maternal.
44:06Maybe I sound crazy, but like I love what she wore and then she took the cape off for the party and I thought that was so, so, so beautiful. I love that. Yeah. I mean, I would also say too, like there's like the mother of the bride that is like obnoxiously trying to take over and be the star of the show. Like obviously that's a don't. Right. But also like you are an important member. Yes, you're up on the stage. Like have it be a moment. Yes. Yes. So feel free to have it be a moment. Like you don't need to undersell yourself either. Like you can look glamorous, whatever. this brings me back to all comes around to cvk her hair and her the dress that's the point like she in her wedding was the way she dressed in real life like even her hair was very understated I don't even like was it off was it it may have been down it was in a bun it was like a messy bun yeah it was a messy bun that's right that's right exactly it was it was very her yeah there's a great follow that I still follow, even though I'm post-wedding.
45:11Her name is Little White Looks at Little White Looks. She's been on the podcast before and she is a bridal stylist and she has an incredible shop my account that she updates. Like I think she's updating it weekly and she's got bridesmaids dresses in every color for every category. Oh my God. I'm going to follow her because pinks, greens, blue. I just like it anyway. Yes. She's got a great. Someone that does good bridal. Yep. She's got guest dresses, black tie, cocktail, beach inspired. And then she also has a whole section of Mother of the Bride and Mother of the Groom dresses. And I would highly recommend following her because I feel like she's got a good handle on that industry if you're looking.
45:47I hope this was helpful, Debbie. Thank you so much for coming on today. You are so wonderful. Thank you. I loved this conversation. And again, you are such a great follow. If you guys are listening right now, do not follow Larissa. Please go follow her. She's Larissa Mills on Instagram and TikTok. And you're going to fall in love with her and her personal style. So yeah, another style icon to follow. I hope I get to see you soon, IRL. And you'll have to come back on the pod again soon. I love having you on. I'll see you soon. Bye. Bye.
46:34Thank you.
Carolyn Bessette-Kennedy is everywhere again but the conversation around her style often misses what actually made it so compelling in the first place.
I sit down with writer and repeat guest Larissa Mills to talk about the frenzy surrounding CBK right now, from the new Love Story series on FX and Hulu to the endless stream of content promising you can dress like her if you just buy the right boots, coat, or sunglasses. Together, we unpack what people are getting wrong about Carolyn’s style, and why it was never really just about the clothes.
In this conversation, we get into:
Timestamps
05:00 CBK resurgence, Love Story and the social media frenzy
07:00 Why “dressing like Carolyn” misses the point of her style
09:00 Larissa Mills on personal style and impenetrable taste
10:00 What women were actually wearing in NYC during the CBK era
12:00 90s minimalism, Calvin Klein, and the “uniform” of the time
14:00 Was Carolyn a style icon in real time—or did that come later?
17:00 The role of aura, presence, and her relationship with JFK Jr.
20:00 Why CBK’s style felt powerful beyond just the clothes
23:00 The difference between copying vs. embodying personal style
26:00 Overconsumption, the internet, and losing individuality in fashion
29:00 How to build personal style through repetition and restraint
32:00 Tailoring, fit, and the reality of making clothes work for you
34:00 Heels vs. flats and the practicality of everyday dressing
36:00 Breaking fashion “rules” and wearing what you actually love
38:00 Editing your wardrobe and developing discernment
40:00 Signature pieces, silhouettes, and building a personal uniform
42:00 Why you’ll never be CBK and why that’s the point
43:00 Introducing “Let’s Get You Dressed” (listener styling segment)
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