The Wonderful Secret Behind Dressing Well on Dates: A Semi-Scientific Essay
I put in a disproportionate amount of work to bring you a longform essay about how we dress to date, while we date, and how to do it perfectly.
A friend, his girlfriend, and I sat on the Metro North on a rainy February night, the Harlem Line taking us back into the city. We passed Crestwood and Tuckahoe; I complimented her Acne Studios jeans and his Buck Mason pants as rain hammered the windows. At Fleetwood, someone asked where I got my clothes tailored. Someone else tapped their umbrella against the ground. A dog shook, spraying its unfortunate owner with musky water. As we neared Fordham, Tremont, and Melrose, my friend asked, “Would you have any good places to get jackets?”
“I like to take him shopping,” she explained, “but I don’t really know all of the spots.” He nodded in agreement. “I need to return some stuff I’ve bought online.”
“We’ll stay in touch!” I had to raise my voice over the automated announcement: This station is Harlem–125th Street. This is the train to Grand Central. “Text me, and we’ll find a time to go shopping,” I promised them. The voice continued: As you leave the train, please watch the gap between the train and the platform.
That was the last time I saw them together: they broke up sometime in the next few weeks.
I had no idea. Over text, I cheerfully offered my fashion help to my friend. He accepted, later letting me know that part of his motivation to redo his wardrobe was to look nice on dates now that he was single and dating.
Ladies: behold! A respectful man! He’s single! He’s dressing well and making an effort to impress you! Watch out, New York!
I was excited to shop with him. I genuinely love taking people to places that I think will suit their style and giving them the friendly encouragement to try something new, letting them know that, “Yes, those jeans fit correctly,” and advocating for taking something they really like to the tailor so that they’ll really like what they’ve got.
I’ll touch on where I took my friend and why, but as I write about where to get a great pair of jeans, where to find vintage shirts, and how to track down good sterling silver jewelry, I can’t stop wondering about the way we dress both in and out of relationships. What should you wear on a first date? How do we communicate, through clothing, that we’re attracted to someone? That we love them? What does that look like when it’s done in a healthy way? In an unhealthy way?
So, dear reader, here’s what we’re going to do. This is a fashion Substack. I’m going to intersperse my research into my questions — over a hundred people weighed in over on Instagram (thank you so much!) — with a few things to keep it engaging.
Anecdotes about my own dating life and relationships to clothing while in serious relationships.
What I’ve bought, worn, and gotten interested in as a result of dating.
Where I took my buddy to refresh his wardrobe: genuinely some of the best spots in New York City that serve all different flavors of people.
Comments on dating in the city.
Scientific papers and general literature about the nature of power, sex, and engagement in relationships.
Sound fun? Think I’m really smart for doing all of this? Stellar. Follow me on Instagram if you’d like to weigh in on future articles.
Dating in New York is difficult. The more seriously you treat the endeavor, the harder it becomes. Techniques vary. The more in-depth approaches vary from spreadsheets (ranking potential partners by quality of date, career, and looks), to the apps ($100 a month be spent on the full suite of dating apps like Raya, Hinge, Bumble, and even newcomer Sitch), and to actively flyering (there’s a great write-up about this over on Mixed Feelings).
I’m single. I go on dates (Gasps! Shock! Awe!), and will readily admit that dating is scary! You’re opening yourself up to judgement, to ridicule, to scrutiny. Just as much as you’re trying to be present, enjoy the moment, and bask in the glow (hopefully!) of someone’s undivided attention, you’re mutually deciding whether or not the other person is suitable — to sleep with, to date, or to make out with in the back of an East Village bar.
Let’s sit with our first question: how do single people — newly single people, in my friend’s case — make a good impression on those they’re dating? I know this isn’t the case for everyone. The “situationship” is as vital to the 20-something experience in New York City as having a shitty landlord, having roommates, or hating (sometimes performatively, sometimes authentically) Le Dive.
In my friend’s selections and in the responses on Instagram, there’s an adherence to popular clothing trends (what everyone agrees is “in” or “good” at the moment). Right now, that uniform is very much inspired by the current hot-boys of movies (Jacob Elordi, Paul Mescal, Jeremy Allen White, etc.): well-fitting vintage shirts, vintage jeans with just a little bit of distressing around the hems, sumptuous leather jackets. It’s all well-fitting, casual-yet-cool, expensive-but-effortless stuff.
So, our first recommendation! Drumroll, please! Regardless of if you’re single or currently dating, one of the best spots for in-the-weeds fashion nerds and “I like to dress well” fanatics is…
My wonderful work-wife Michael Smith (love him!) agrees: it’s the safest spot to send people at all ends of the fashion spectrum. It works well with what’s popular (stacks on stacks of carefully sized vintage Levis, in-house shirts that fit just right, and a mind-boggling selection of silver rings, bracelets, and necklaces) and what’s timeless (well-made military jackets from the ‘60s, vintage Schott leather jackets, shirts simply tagged as “perfectly faded white shirt”). If you show up here and tell me you can’t find a single thing that interests you, I’ll tell you to get your eyes checked.
My friend and I made this our first stop. It’s the perfect place to go shopping on both ends of the spectrum: basics to build a foundation, eye-catching, unique pieces to be the ornament on a well-crafted, thoughtful look. As he shopped, I kept an eye out for who else was in the store. Surprise, surprise, there were a lot of couples.
“This is so you!” declared a short brunette woman as her boyfriend sheepishly grinned in a vintage trench coat. “You’d look really hot in this,” said one man to his partner, holding up an ‘80s collegiate ringer tee. “How do I look?” asked my friend trying on a pair of Levis 501s. “I like the way they look with my shoes.”
The jeans did, in fact, look really good with his shoes.
I noticed that basically everyone in the store was really well dressed. Outfits were intentional, manicured, and rarely gauche. Front General is not a singles mixer, but I still found myself chatting with a well-dressed woman about her (really cool) Paul Stuart pants. We exchanged Instagrams.
I got to thinking about my white t-shirt and jeans; my beloved uniform! What do these things say about me, Mr. Single Man in his 20s in New York? What did my friend’s new purchase of 1990s Levi’s and a linen Ralph Lauren oxford say about him? A writer-in named “Buck Ball” gave an explanation:
“When I’m single, [my clothing choices] are a wishful amalgamation of what I think is attractive about me at the time. Dating multiple people means that you just have to apply the same method [of dressing for a partner] to multiple partners. Dating multiple people in my experience isn’t a great time to “try something new.”
“What do you wear on dates?” my friend asked. “What I’ve got on right now,” I explained as I gestured to my white shirt and jeans. The combo’s served me well on almost every date I’ve been on.
I wear my uniform because it’s comfortable. It looks good. I have broad shoulders, a good chest, and long legs; a $12 Uniqlo shirt I bought in 2018 and some selvedge denim show them off well. My friend quoted a photo of John Mayer and a collection of the current, aforementioned hot-boys of the year. “Paul Mescal shorts” are apparently a thing.
I didn’t think the second stop of the trip would fit the bill at that point, so we skipped it. It remains a spot that, while pricey, usually stocks some pretty stellar vintage (yet still formal) men’s clothing:
It’s a great, little store with stuff for both men and women. I wouldn’t be shocked to hear that they sell pieces to the it-boys’ stylists — Hermès polos, oversized but not schlubby; ‘90s Helmut Lang — the apogee of minimalist, toned-down basic world — vintage Armani, Prada, etc… the list goes on.
Instead, we set out for Fine and Dandy, a pair of stores in Hell’s Kitchen where I worked in 2017 (though it was only one store at the time). Matt and Enrique keep a fantastic variety of menswear, both in the classic and modern senses, and they’re stellar stylists. My friend gravitated towards more oxfords and tried to find a dress shirt with a banker collar. Unfortunately, Matt and Enrique didn’t have any that fit the bill, but that’s the reality of vintage shopping.
I had to run back uptown and left my friend with a long list of other stores he should check out (head down to the bottom of the article for that list), but as I sat on the 1 train, I started thinking about what similarities lay between me and my friend. We both, obviously, thought about what we were wearing and why we were wearing it, but we’d arrived at fairly different conclusions. Him: oxfords, linen pants, Nike Blazers, and Members Only jackets. Me: Daft Punk t-shirts, selvedge denim, the same old pair of boots, and an eclectic mix of sweaters and knitwear. We shared sensibilities, as two single guys in New York, that superseded the clothes we wore.
We aren’t wearing the exact same things, but we signal the same thing: I thought about what I put on today. I made an effort.
Our clothes fit correctly. Shirts aren’t stained (sometimes, in my case). We can put together a good look. We’re single! We’re capable of taking care of ourselves! You’d be getting a boyfriend (or someone to sleep with, or someone to date, I don’t mean to assume what anyone’s after) who’s capable of doing that!
So, the answer to my first question: how (and why) do we dress when we’re single and dating? Some people say men (in particular) dress for the female gaze (this is a heteronormative perspective, I’m aware. This is what I can speak to and don’t feel qualified to do otherwise) to attract and hold the attention of potential romantic partners.
This doesn’t change the fact that a lot of men struggle to dress for the female gaze because they incorrectly interpret or understand the female gaze: my wonderful friend and editor Lindsay let me know that both she and a lot of her friends agree on this point.
Others postulate that men dress for other men, aiming to impress their peers and those they admire or compete with (for attention, "clout," Instagram likes, or whatever suits your fancy). Others (quite literally dozens in the DMs) proudly state they dress only for themselves.
I don’t think the answer fits neatly into any of these categories exclusively. More than one thing can be true.
Clothing changes your capability to think, process, and handle information, both inside and outside of a romantic context. A 2015 Columbia study assessed social commonality, social closeness, intimacy, power, and two other potential mediators (mood and arousal) through participant’s engagement with formal clothing. The study found that social commonality, social closeness, and intimacy are associated with decreased social distance, whereas a perception of power is associated with increased social distance: formal clothing (things you’d likely wear to a job interview) tends to increase feelings of social distance, while informal clothing (wearing things that you feel comfortable in or that feels ‘like yourself’) tends to decrease it.
Regardless of who you dress for — while single, while in a relationship, while in the vexing in-between of a situationship — the increased comfortability and confidence of dressing “informally” (that is, more like yourself) can increase how close you feel towards others. And yes, that might still mean suits and ties: informal in this case is what feels most ‘like yourself’. Two things can be true!
Further, it doesn’t really matter how you dress (more on this later) while dating. It’s not a stretch to say that confidence is sexy. Ready for this? Take a wild guess as to what, if anything, increases feelings of self-confidence, mood, and general behavior?
Being intentional in the way you dress! Selecting an outfit with a degree of discernment!
Let’s do another one! What — and really rack your brain here — increases your sense of identity, belonging, authority, or general self-assurance?
The symbolic meaning that people themselves put into their clothing! 88% of people in a 2024 survey published in Global Scientific Journal agree!
There’s anecdotal evidence too: writer-in mxrlon.z comments that, “At the end of the day, I would personally worry more about staying in good shape and wearing nice fragrances for my partner or date rather than dressing in a certain style that I perceive to be more attractive.”
Now, clothing, fragrances, or being fit aren’t the only factors that drive changes in mood, but the point I want to hammer home is that it doesn’t matter what you wear (in most cases. I believe anyone reading this Substack is capable of putting together a good outfit) but rather whether or not that clothing 1) holds meaning, 2) is selected with intentionality, and 3) makes the wearer feel confident!
Wham! Bang! Scientific evidence of what everyone was telling me! Something I can hold above my head and wave around in triumph! I realized that, unconsciously, that’s exactly what my uniform does for me (see my language about my shoulders, chest, etc.). It makes me feel confident! The necklaces I wear hold personal meaning (they were given to me by my wonderful friends), the boots I wear are a beloved possession (I bought them in 2018 while working on farms in Australia), and the shirts I wear, in some way, connect me to a past version of myself. They make me feel like me.
This drive can be endogenous (originating within oneself) or exogenous (coming from outside sources, or perceived as such). Vw_gabe explains that they definitely “try and dress a little better for my girlfriend. She’s never asked me to, but I definitely feel like if I dressed poorly, she’d pay more attention to guys who [do dress well], as shallow as that sounds.”
I think that’s a totally valid concern, and it loops back well to my point about confidence: whether or not that thought is the reality, the confidence that comes from dressing up and making an effort helps dispels the anxiety surrounding Gabe’s partner wanting someone who would. Nobody wants to date someone who can’t make an effort!
We’re all insecure about something. Clothing can’t solve those insecurities, but it can definitely make them worse. Anybody who’s gone shopping for jeans knows exactly what I’m talking about. Alexander McQueen described his couture as “putting armor on a woman. It’s a very psychological way of dressing.” Now, McQueen wasn’t waxing poetic about journal publications on Substack (unless I’m mistaken), but I think we’re saying the same thing: armor covers weak points, insulates from unwelcome blows, and serves as a symbol of an oncoming battle.
What better to cover your weak spots than an outfit you love and know you look good in, and what better a place to wear it than a first date, where you’re trying to show off the best parts of yourself and obfuscate the less-than-savory ones?
What better to distract than with a cool shirt, a fun jacket, or jeans that compliment your figure? Even better: what better way to form a connection?
We’re on our second question, folks! How do we communicate, through clothing, that we’re attracted to someone?
I called my friend Tanner Dean to ask him about my various theses regarding dating.
Over the course of a lovely, 45 minute conversation, he told me the story of a first date he’d gone on with a film major. To impress her, he picked out a vintage t-shirt from the Great British Film Rally. “It’s a cool shirt,” he explained, “I still wear it now, so it’s not like I wore it only to impress her. I just thought it would be a nice touch that showed that I noticed her interests; the outfit looked like something Matty Healy would wear because The 1975 was one of her favorite bands.”
Big cheer! Men who listen! Crowd goes wild!
I got to thinking about things I’d bought while dating to — let’s be honest for a second — impress or connect with the people I’d dated. Tanner wasn’t some anomaly.
I wasn’t ever the biggest Chemical Brothers fan (though I have, on many occasions, spoken of my love of DSquared2’s MetaMorph runway show, which is scored by their song, Go), but I picked up a vintage tee or two when an ex mentioned that she was a huge fan.
No grand revelation here on the second question, but it’s good to lay out: listening to or noticing your date’s interests and communicating that, yes, I think that’s cool, and, by proxy, you are cool and interesting and worth paying attention to is the way you communicate genuine interest.
It’s affirming to feel that you and your passions (especially when they’re reflected in what you wear) are interesting to those you date. I personally think that — alongside confidence — having passion is an incredibly enthralling trait.
Is this observation supported by science? Not really. Shit. Well, I can't be right all the time. A massive (15,000 participant!) study in 2020 found that, women around the world, on average, indicated preferences for an ideal long-term mate with greater financial prospects, whereas men on average indicated preferences for more physically attractive mates.
That study didn’t select for 20-somethings dating in New York exclusively. However, the European Journal of Personality published a study by Zhao et. al. examining speed dating sessions with 1,145 participants. They found that four traits ranked as most important for overall attraction: kindness/understanding, intelligence, creativity, and (pause for dramatic effect!) confidence!
Isn’t it freeing? To know that, as long as whatever you’re wearing makes you feel confident about yourself, you’re going to be more attractive?
I’ll use another lovely anecdote as inspiration for you, readers: some of the most beautiful, attractive, and generally trend-setting people in New York (and abroad, for that matter) wear some fuck shit. I’m talking generational, cataclysmic, earth-shatteringly bad fits — in concept. Ever heard of a terrible outfit being good because the person is hot? Hot is a mentality. Hot is a mindset. Hot is a lifestyle, a conscious choice to say, wholeheartedly, unabashedly, and truly, “I’ve put that shit on.”
So: how do you facilitate a relationship through clothing? Dress for a date, dress for a hookup, dress for yourself — it doesn’t matter! Dress in whatever makes you feel confident.
Now that you’ve got the partner: how do we change (or not change) what we wear while in a relationship? How does having a partner — someone to love, adore, cherish, and dote over — influence your decision-making?
I moved to the city while in a long-term, committed relationship. I was convinced it would last forever. We made plans to meet at a coffee shop on a beautiful September afternoon. I showed up in a white t-shirt, my jeans, and a pair of Guidi boots. She broke it off. Gut-punch. Tailspin. Spiral.
We did the classic “hey, I’d love to come get my stuff” song and dance. It took me months to get everything back. To be honest, I forgot some of what she’d kept (I didn’t forget the knitwear, really good vintage t-shirts, or the custom dress shirt that got returned smelling like someone else’s cologne) but, as I opened a big cardboard box in February of 2024, I realized: girlfriends do funny things to your wardrobe.
They shrink them, for sure — t-shirts go missing, hoodies are “borrowed,” your jeans become “boyfriend jeans”… your clothes aren’t just your own anymore.
Your options get limited, sometimes. Many of the writers-in commented on this. ar1th1_ explained that they “tone it down a few notches around my parents, her, other family members, etc. — there are a lot of stigmas around people who dress in darkwear and I wouldn’t want to come off as ‘emo’ or ‘uneducated’.” gimbal_locked_in explained that when she and her boyfriend are heading to certain events, she “[throws] shit on the bed for him to wear.”
I’ve always had a hard time with being told what I should wear. I had an ego about being a “fashion guy” and thought I knew better than one of my exes. I showed up at her mom’s house (to meet her for the first time) in a tie-dyed t-shirt and cutoff jean shorts. Her mom thought I was a deadbeat.
Say what you will about judging people or making assumptions, but in hindsight, that was a horribly stupid decision. I got defensive about it, made every excuse in the book, and tried to justify my choice, but the fact of the matter is: sometimes, regardless of your opinion, you’ve got to listen to your partner and play by their rules.
I’m a firm believer in loving the person in front of you. That means not loving an idea of someone, what someone could be (and withholding love until that’s reached), or who someone was. I used to think that included the way I dressed: “I should be accepted as I want to be at all times.” And, to a certain extent, that’s true! However, the more mature view (or, I think, the one I’ve grown into) folds in the sensibility of: “This matters to you, therefore, it matters to me.”
There are endless videos on TikTok of creators explaining how to get a boyfriend to dress well. Some of these videos feature genuinely good advice — shirts that fit, formal shoes, skincare, etc. — but others veer into needing to psyop a partner into integrating basics (yeah, quality basics!) into a wardrobe.
You can’t love, bully, force, or coax someone into changing something about themselves. Wardrobes are a little bit easier, but still fairly impenetrable: my dad owned the same, ill-fitting suite of khakis and t-shirts until my mom literally threw them away and bought him new ones.
Trying to sculpt a partner’s image is, in some way, a form of control. There’s a long history of control through clothing. Take, for example, the corsetry of Victorian England, which made women physically feeble and (often) ill that they couldn’t question, challenge, or otherwise recapture control from their male partners. This manipulation of one’s partner through clothing or body standards hasn’t disappeared over time.
Evan Stark explains in his book, Coercive Control, that men in particular, perpetuate abusive patterns through regulation and dictation of their partners’ daily routines (which includes what they wear, when they wear it, etc.). Logically, this makes sense: if autonomy in clothing choice is what makes you feel comfortable (think about our earlier discussion of reduced social distance), robbing someone of that autonomy drives feelings of isolation, unease, and general anxiety.
More recently, Fruchier et. al. published a paper titled “Satisfaction with partner’s appearance, body criticism, and relationship quality in heterosexual couples: A dyadic study,” in which they explain that individuals who reported high levels of body criticism from their partner perceived lower partner satisfaction with their overall appearance. Basically, respondents associated negative feedback on their bodies with lower satisfaction with their own overall appearance: this perception was directly linked to poorer relationship quality.
It’s not a stretch to say that clothing is intimately linked to appearance — historically for women, and increasingly for younger men today. It’s all tricky! You want your partner to dress better (for an event, to show that they’re making an effort, whatever reason), but you don’t want it to come as a personal attack! So, what to do?
The best approach, especially with a partner who’s open and willing to change (people you should be with!), comes from a place of love and intimate understanding. Ives Barrera explained their experience in buying clothes for their partner and their mentality:
“I bought a purse for my girlfriend, and she didn’t end up wearing it. When I asked her why, she responded that it ‘looks like something that you would want.’ [It changed my] perspective on gifting clothing especially. It takes me longer to get my partner a gift, and I find myself thinking ‘Is this something my partner likes or something I like?’ I want to make sure she gets utility out of whatever the final gift is, rather than trying to sculpt or dictate her image.”
This sentiment was mirrored repeatedly in the DMs. Healthy relationships work because people are willing to listen, make concessions, try new things, and make efforts to continue to love and appreciate their partners.
_glocklan wrote and explained that, “I think that, because my partner and I are aligned on the same [interests and values], she and I influenced the way the other dresses without realizing it. It’s a very good thing because I think it shows we care for each others’ interests and tastes and want to live as a single unit.”
I think paige_bradbury puts it perfectly: “Style is what helps attract people to one another, platonically and romantically… it can be a great conversation starter.”
Here’s my big realization for you, dear reader! The grand finale!
It all doesn’t fucking matter! What I’ve been trying to convince you of, this entire time, is that clothing is all a proxy for being confident, showing you care, and making someone feel respected and desired!
Being in love entails a reduced distinction between the self and the romantic partner. Aron & Aron (a duo of researchers) investigated partner overlap in relationships and found that in close relationships — especially romantic relationships — the self expands to include aspects of the other: think about Kylie Jenner showing up and showing out for Timothee Chalamet’s Knicks.
Getting validation from your romantic partner, hookup, or date is an amazing thing. It’s a confirmation that you’re on the right path — that your effort, your values, your status as a prospective partner were worth the time!
I don’t have perfect answers for all of my questions. I gave you some pretty good explanations, but I can’t hand off a panacea for anyone looking to dress perfectly on a date. What I can do is give you a fantastic list of places to start looking, and the encouragement to dress in what makes you feel comfortable. Keep in mind that the way you present yourself isn’t going to meet all the marks for everyone (like me in my poorly-picked tie-dyed shirt and jorts), but it will facilitate you meeting someone with that shared interest, passion, or sensibilities. You’ve just got to be patient.
Thanks for reading! I’d love to continue to grow the Substack, but I can’t do so without your help. Please – share the article, enjoy the list, and drop me a message. It means the world to me.
Retail Stores for Clothing, Jewelry, and Generally Well-Dressed People
Silver Jewelry:
Stock Vintage: also has leather jackets, cool boots, and an AMAZING selection of vintage tees that (I believe) Jacob Elordi’s stylist has picked through on occasion
Bungee Space: small selection in one of the cases, but they’re simple and pretty rings without looking too crazy. Good to go try on and they won’t break the bank. Also some fun clothing from smaller designers.
Self Edge: BIG selection of really cool silver jewelry. Also have crazy cool horsehide leather jackets that are hyper expensive but fun to try on.
Lara Koleji: sometimes have a good selection of silver in their little case. Favorite store of a lot of NYC fashion boys. Pricey on the clothing front. Also have really good sunglasses.
Clothing:
Wooden Sleepers: probably going to be your best bet for oxfords or “menswear”-ish stuff. Insane variety.
Crowley Vintage: also about a billion options for sweaters, oxfords, etc.
Stella Davis: I think they’re still doing western stuff, but I’m not sure. Worth checking out.
James Veloria: more women’s clothing than men’s, but there are a lot of gems here. Unfortunately, they rarely have things in a 48 or 50.
Pants (in particular):
Hate to say it, but this is a tailoring game. I own $4 pants and $400 pants, and they all have gone (immediately) to the tailor. Just pay attention to fabrics and make sure they sorta fit (just a little big is fine). Pop into a tailor and ask them to help you make them fit (I can come too and talk to the tailor about what needs to be done) but what’ll help is a clear idea of HOW you’d want them to fit.
Other good stores/spots:
Alfargo’s Marketplace: Fun spot with a lot of good “menswear” at fairly reasonable prices.
Blue in Green: Japanese Americana. I operate under the rules that anything you find in here, you can find 30-50% cheaper online.
Standard and Strange: More of that expensive-but-really-good menswear stuff. Think pricey selvedge denim and flannels
Cueva and Ven Space: expensive boutiques but good to go to and try on new and exciting stuff.
Huge thanks to everyone who helped on this article and a particularly large shout-out to my fantastic editor, Lindsay Jost.
It means the world to me when people engage with the things I write, and Lindsay’s got to read all of this stuff before it looks pretty (and makes it look pretty!).