Fashion Lovers

Four couples talk about navigating personal style and how they overcome the quote-unquote swag gap.

  • Written by: Alyssa Vingan

It’s a weird moment in culture to be a single, open-hearted woman searching for love. Look no further than recent headlines surrounding dating and romance for proof: Vogue is earnestly asking whether having a boyfriend is embarrassing now. We’re living through a “sex recession,” as adults are getting laid less than ever. Gen Z might be afraid of sex. In the gender war, everyone is losing. Heteropessimism is at an all-time high. People are avoiding intimacy at all costs, having emotional affairs with ChatGPT. Over on TikTok, those who do dare to date are running strict programs to weed out bad behavior and discussing dealbreakers like the dreaded swag gap. What’s a lovergirl to do?

Despite all of this, I haven’t given up hope. I’m no quitter! I’ve been ghosted, slow-faded, led on, lied to — all par for the course in modern courtship. In moments when I fear I might be losing faith, something that keeps me going is watching love blossom around me. Hearing about a friend’s new crush warms my heart as if the crush was my own. There’s a reason rom-coms and romance novels are popular right now; yearning is so back! This extends to my parasocial relationships, too. Seeing famous people whose careers I follow closely find a partner — especially one in aesthetic alignment with them — feels personal to me. I’m not afraid to admit I ship it.

My Harry Styles-focused group chat has pored over his paparazzi pics with Zoë Kravitz over the past year. They complement each other stylistically and seem completely in sync when it comes to their taste. You’ll never catch them outside without their vintage Levi’s, well-worn band T-shirts, expensive knits, relaxed trousers, and some beautiful outerwear. You just know The Row loves to see them coming. There’s no red carpet arrival I look forward to more than A$AP Rocky and Rihanna, and no couple on the planet is more perfectly matched from a swag perspective. I swooned when Timothée Chalamet thanked his partner Kylie Jenner at the Critics Choice Awards, but even more when they both showed up at the Los Angeles premiere of Marty Supreme wearing orange Chrome Hearts. They seem to be having the time of their lives.

I rolled my eyes the first few times my FYP served me “swag gap” content, but the longer I think about it, the more I realize TikTok was onto something. I never really took personal style into consideration when looking for a partner. I was with my ex-husband for 14 years; in that time, I almost never borrowed an item of his clothing or had a meaningful discussion with him about fashion, despite it being my profession. In hindsight, he rejected many bids for connection over one of my main passions, which irrevocably damaged our relationship. It makes sense to me now that his indifference to anything style related bled into other areas: we didn’t want to see the same movies, read the same books, listen to the same music. I learned the hard way that a lack of curiosity about your partner’s interests slowly but surely breeds contempt.

In the five years I’ve been single since my divorce, I’ve still mostly considered personal style to be superficial — a shallow thing that didn’t really matter in the grand scheme of compatibility. Only recently have I had a change of heart. Last year, I briefly dated a deeply swagless man. He checked a lot of my other boxes, much more “important” ones, so I turned a blind eye to his excruciatingly tight jeans and unironic trucker hats. After a few months, it became clear that we would never work out for myriad other reasons, but looking back, the two were related, even if tangentially.

Having personal style reflects a strong sense of self and confidence. If you don’t love yourself, you can’t possibly love someone else. How you show up in the world from an aesthetic standpoint says a lot about your personality, your value systems, your curiosity, your creativity, and how easily you conform, which are all crucial to notice when looking for love. If you pay close attention, the answers are often written all over your date’s outfit. For better or for worse, your partner is an extension of you, and how they choose to present themselves matters.

In the spirit of Valentine’s Day, I asked four of the most well-dressed couples I know a little about how their shared and individual senses of style factor into their relationships, and how a love of clothing has brought them closer together.

The couples:

Megan O’Sullivan (writer and cofounder of Byline) and Aidan Caldwell (set designer), together for 2 years.

Telsha Anderson-Boone (influencer and entrepreneur) and Justin Boone (stylist and creative director), together for 6 years.

Sameer Sadhu (music label executive) and Alex Sadhu (cofounder and CTO), together for 10 years.

Michelle Li (creative and writer of newsletter Good Fantasy) and Brendan Chareoncharutkun, (founder of Uncle’s Thai Food), together for 1.5 years.

When you were dating, how much did sense of style matter to you when choosing a partner, or play into whether you were attracted to someone?

MICHELLE

For me personally, it didn’t play a big role. I’ve dated people in all kinds of industries and with different levels of swag. I cared more about them having a point of view, or a vision for themselves — not necessarily that they had to be up-to-date on trends and be super cool.

BRENDAN

Sense of style for me really is important. I think it transcends and permeates in different ways, like taste. How you dress is often associated with where you eat, or how you travel, and what you put value towards. Somebody’s style should really resonate with me, because I feel like that means we’re more in line with how we would want to live and how we would want to spend our money.

MICHELLE

Unless you’re with someone, and they’re like, “Yeah, I just don’t care about what I wear, that’s not important to me.” That’s okay with me. If they are self aware and accept that their style is just not a priority. I respect that.

MEGAN

It did matter to me because it’s just a certain energy — it just means you have creative interests. Aidan has a lot of swag because he has interest in clothing and skateboarding and culture.

AIDAN

I think it shouldn't matter too much, but I do feel like having interests and showcasing your interests through your style is certainly attractive. I feel like both Megan and I showcase a strong sense of self in our style.

TELSHA

For me, style mattered a lot prior to dating Justin, and that was partially the issue. I was so focused on the clothing, I wasn’t focused on the person. And then I switched my mindset: I stopped thinking about the clothing and focused on the person. With Justin, luckily he came with both, which is really fun — I stared at his face and stared at his heart and stared at his fit and I loved it all equally.

JUSTIN

For me personally, style and swag mattered, but it wasn’t something that I was definitive on. One of the biggest things that did attract me to Telsha in the beginning, before we even spoke, was how dope she was, how stylish she was, how cool she was in that regard. It’s a big pivotal thing in our relationship now; people look at us for style, for influence. I think that we inspire and influence one another, which is cool. I style her for a lot of her projects, and she’ll look at me crazy if I put on something that’s a little too out there.

Telsha and Justin

Did you bond over fashion and shopping in the courtship phase?

SAMEER

We started dating around the same time I started getting into clothes. We were into finding things and talking about things that inspired us. We found Bode together and went to their studio together in 2017. Because she lived in New York and I was in LA, for a certain period of our relationship, a lot time was spent walking around downtown and shopping.

ALEX

Our first date was at a museum, our second date was at a show. Then we did a traditional date as our third date. We were always engaging with that — not just clothes, maybe aesthetics. But we definitely were both interested in similar things in terms of finding inspiration.

TELSHA

Funny enough, our first conversation was about a vintage T-shirt. At the time, Justin was reworking T-shirts — he specifically had a Jesus tee he posted. He told me to go to Etsy to buy it, which I thought was rude. Three days later he posted again; it was a link and it was his business, so I bought it, a $170 T-shirt. I purchased it and now it hangs in our son’s bedroom. We’ve been talking about clothes since day one. From T-shirts to babies, literally.

JUSTIN

A lot of our conversations in the courtship phase, and even still now, definitely circled around fashion. We’d spend nights in bed or even random afternoons just talking about what’s going on in fashion. We watch red carpets together. We talk about the most recent shows. We’ll sit down in the living room and play a fashion show in the background — we'll watch it, but we'll also be working. It’s really cool for us to have that bond. I think it would be hard if we didn’t understand each other in that way, because it’s such a big part of our lives.

Meg and Aiden

Do you borrow each others’ clothes? When you’re making a pricey purchase, do you take into consideration whether your partner will also be able to wear it?

SAMEER

For sure. We bought a sweater from Stoffa the other day, and it fit both of us. I got it for her as a gift, and then I stole it from her literally four minutes later.

ALEX

We have a lot of [soccer] kits. T-shirts we share a lot of, too. We’ll buy a T-shirt at a show and we’ll get it to fit both of us.

SAMEER

Alex loves buying merch from small cafés and things as we travel around. I’ll get a massive size and then I take it to the tailor and get it cropped so that we both can wear it.

MEGAN

I mostly borrow Aidan’s clothes, like bigger jackets … from the beginning I’ve taken his T-shirts, hoodies, or crewneck sweatshirts.

AIDAN

We definitely think about whether we will share something, but also if you’ll be able to wear it or even want to wear it. I think that definitely does impact my shopping in some way. Probably for the more goofy, risky purchases. The stuff that you don’t necessarily need for yourself, but you want to share with someone. If I’m not gonna have the confidence to wear this, I know you will.

Brendan and Michelle

Do you ever consciously dress alike? How about unconsciously?

BRENDAN

We travel a lot together, and oftentimes we’ll think about something we want to wear on a trip, and we’ll buy a few pieces to go on the trip. When we’re thinking about, you know, going to Thailand, we want to buy things that we could both wear together at the beach. Or matching an airport fit. It’s super Asian, but also really fun.

MICHELLE

I feel like I’ve unconsciously started dressing like Brendan in some ways. My friends are always commenting about how I wear jeans now, which I never used to do. Brendan is such a jeans person, always showing me different vintage jeans he’s finding. He has such an eye for denim that it’s changed the way I look at it. I definitely wear more jeans, and vintage T-shirts, and have more of a boyish style.

BRENDAN

I think I’m so comfortable wearing the same thing every day, particularly clothes that are unassuming. Dating Michelle, I really wanted to start having more fun with my clothes, so I explored more colors and materials. I’m a little bit more open to buying things that I wouldn’t typically want in my closet, and then giving it a try, and sort of adjusting my style from there.

MICHELLE

We don’t consciously dress alike. We actually have some of the same shorts or something, but in different colorways. Sometimes we’ll both wear it by accident, and it’s kind of funny. But Brendan doesn’t like to dress in the same item. You don’t want a twin.

MEGAN

Something I will take from Aidan is a Supreme hoodie, and we both can’t wear a Supreme hoodie at the same time. Or we’ll accidentally wear the same color palette, like blue pants and a brown sweater or something, and be like, “OK, one of us has to change.” I don’t know if that’s something that happens when you live together, like subliminal telepathy. But it does seem to happen more often than it did in the beginning.

AIDAN

I definitely would say 100 percent, not consciously. 100 percent unconsciously.

ALEX

It literally happens all the time.

SAMEER

We were at dinner the other night wearing the same thing.

ALEX

We’re both wearing jeans and a Stoffa sweater. I mean, it’s winter, like, fair. What are we gonna wear?

SAMEER

But it’s very unconscious.Alex: We have had to change before because it looked stupid. Like, this is too much.

Brendan and Michelle

How does your personal style differ from your partner’s? How is it similar?

BRENDAN

We buy a lot of similar clothes, and we definitely share a sense of style. If she’s really into something, like a style of a jacket, I might buy a similar style jacket.

MICHELLE

I think that being so intimately close with someone and seeing how they get dressed every day, what things they’re considering buying, how they’re shopping ... It helps me see myself differently, see how I want to dress differently, and reconsider my own personal style, which I think is really fun. It’s really sweet because we can talk about style, and we both shop similarly. If I’m like, “Oh, I want a yellow T-shirt,” you’ll be shopping for vintage T-shirts and if you see something that you know I might like, you’ll send it to me. It’s a fun way to see how Brendan interprets my style, seeing what you think I might like.

BRENDAN

When you’re searching on eBay or Grailed or Depop you come across so many good pieces that are not your size, and you just wish you could get it for somebody, or you wish it could be yours. If I see a really good vintage T-shirt, I’ll just send it to Michelle, or I’ll just buy it and surprise her with it.

MEGAN

Aidan has a lot of skate influence in what he wears. So it’s inherently more urban, a little more boyish. I definitely can go both ways. I like to dress with baggy jeans and a T-shirt. But then I also love to wear a super girly dress. I think it’s different in that we have different influences.

AIDAN

I think my personal style is really attached to where I’m from. Being from DC, which has a style scene that’s unique to other places; a little bit off kilter, a little bit off the beaten path as far as thought of as a “fashionable” city. It definitely makes my personal style more wonky than what I think to be Megan’s pretty well researched and well thought-out style.

MEGAN

I wrote this article for Vogue back in 2022 about dressing like your crush — dressing like the person you’d imagine yourself being attracted to. And mine was very boyish, skate influenced. I would say that you are the crush that I like to dress like sometimes.

Sameer and Alex

Do you ever give your partner feedback on their outfits? How is it received?

MICHELLE

[to Brendan]You do, but you’re very sensitive and open — you’re very kind about it. Then you always let me make the final decision, which I think is really nice. You’ll give your feedback, but I feel very comfortable still exploring my style without feeling any judgment from you.

BRENDAN

Michelle really wants to push the limits of my style. I really love to stay in the very masculine, very uniform. Michelle’s tried to put me in, like, pink sweaters, cropped tees. And I just don’t feel like myself. I don’t think I could ever wear clothes where I don’t feel like myself.

AIDAN

I would never give feedback per se on a full look, but maybe I would say that you could style this with that.

MEGAN

Aidan’s really big on layers. I can be more simple and direct in what I’m wearing. So he’ll be like, “Oh, I have this idea for something you could add into that.” It’s positive feedback that’s constructive for both of us. It’s like, “Oh, that looks good. What if you added this?” I’ll be like, “Those jeans you tried on look good on you because they’re a different fit than you normally wear. Maybe that’s something to branch into.”

AIDAN

Which I appreciate because you’re feeling pretty vulnerable when trying on jeans that are a little bit different than what you normally wear.

MEGAN

I think we like to encourage each other in a direction that we see each other looking really good in.

SAMEER

I think it’s really cool to see us push each other, and have a sounding board that is very thoughtful. You always want to be your best self for the other person.

ALEX

Sometimes if I’m asking his opinion, he’ll be like, “You always look good!” And that’s when I know I look bad.

SAMEER

I remember [in the beginning] when I bought a pair of slim white Acne jeans, and I’ve never heard the end of that.

ALEX

Oh, my gosh. I’m on a trip with a friend of mine and he sends me this freaking photo of him in white jeans. I was like, “I leave the country, and this is what you do!?” He had to return them immediately.

Has sharing a love of fashion has brought you closer over the years and why? What has it taught you about one another?

MICHELLE

There’s things that we can both learn from each other, and that brings us closer together. We both respect each other’s style. When there’s the respect and the curiosity to learn, I think it can really connect you and make you a lot closer … just have a deeper understanding of each other, too.

BRENDAN

I never really paid attention to runway shows or all the things that go into a collection. Having Michelle as my girlfriend, I really get to understand the thought process … how to think about clothes less like individual pieces and how I feel about them, and more like a collection of work, and in a more artistic way. I feel a lot smarter and more informed when I’m looking at clothes.

MEGAN

I think it’s a point of reference. It’s fun for us to be out in the world and be like, “Oh, look at that person’s outfit.” Or, “That’s interesting, I never thought about wearing that with that.” It’s less about the clothing itself and more about noticing things around you and being able to converse about it. I respect Aidan’s point of view on it, and it’s good to have things that you respect about each other.

AIDAN

I feel like we’re able to get closer from, not necessarily fashion and clothing, but the references and things that surround them — the feeling that it gives you.

MEGAN

Something I love about Aidan is that he can really tap into a sense of nostalgia and emotion through clothing — what was worn in a music video, or what was worn in a skate video. And that, to me, is less about an interest in clothing and more about, like, a capacity to feel something. And I think that’s what I’m really drawn to, and maybe clothing is the vehicle, but nostalgia and emotion is really what’s at the heart of it.

ALEX

It’s one of our shared interests; it’s brought us closer because we’ll go shopping together, and we’ll make a day of it. It’s one of the things that we enjoy chatting about. We’re both inspired by new stuff and we’re each always changing how we dress.

SAMEER

It feels like we grow together, and this is one of those vehicles that’s part of it. We might not always agree, but it’s been a key thing — just being quizzical and interested in it.

Alyssa Vingan is a writer, editor, and host of The New Garde, a podcast about the future of the fashion and beauty industries.

  • Written by: Alyssa Vingan
  • Date: February 13, 2026