We’ve all been there: You’re on a Tinder date and the guy shows up wearing a very, very large scarf. Do you run? Or do you stay and pray for “good conversation”? You sort of hate yourself for caring about your date’s style malfunction. But you care. You really care. Of course, there’s truth to the old adage that clothes don’t make the man. True love is about connection, trust, intimacy, and compassion. And yet, no one wants to date someone who looks like shit.
Style is important to me. It’s sexy, and it makes being conscious far less boring. To quote the iconic street style photographer Bill Cunningham: “Fashion is the armor to survive the reality of everyday life,”and everyday life is difficult enough without throwing a deep V into the mix. If you’re at all sartorially inclined, can you date someone if you hate their style?
A few years ago, in a momentary lapse of judgement, I let a friend set me up on a blind date. The guy sounded great on paper: an architect, well traveled, had built an orphanage in Mexico (or something low-key colonial like that). But then he showed up wearing jeans that gripped exclusively around his thighs and a tank top with confusingly large arm holes. Red flag(s). Halfway through dinner, he told me that he’d done ayahuasca more than 60 times. I was like, “Dude, I already knew that—I could tell by the little rock in your braided anklet.”
It’s often said that it’s both misguided and superficial to judge people by their clothes, but I think you can tell a lot about someone from what they’re wearing. The way we dress is part of how we construct our personal narrative. Our clothes are the most visible manifestation of our desires and our identity, and I don’t identify as someone who dates a man with a pocket square. (Instead, I dress like Elle Woods at a sex party, but in a way that attempts to be meta and self-aware. I think it’s working?)
My friend Clara agrees that style and substance have far more in common than we’re led to believe. Clara worked in fashion in New York until her recent move to Los Angeles. Initially, she was excited about her new, aggressively meditative, Prius-sponsored, dad-jeans L.A. life. But as soon as she started dating, she was hit with style culture shock.
“L.A. is like an early retirement resort,” Clara told me. “If you just wore workout shorts and flip-flops every day, you’d be fine. Most people don’t even own real pants. I thought we’d made fun of fedoras so much that no one would dare wear them, and yet, in L.A., you find every form of fedora and its cousin. And beanies in 90-degree weather. It’s like, you’re a 38-year-old man, why are you wearing hats?”
Clara’s friends tell her she’s a snob—that if hats are a deal breaker, she’ll never date anyone. But she argues that style differences can be representative of larger incompatibilities. “If I met an amazing guy and he wore a terrible hat, I could probably work through that,” she said, pensive. “But we don’t make style choices in a vacuum, and it’s hard to take someone seriously if he’s wearing a shirt that shows his nipples. If you’re looking for a life partner, then you don’t want to date someone with a Burning Man wardrobe and a Burning Man house and Burning Man life goals.”
How true. And yet, you’re never going to find a 100% match. Like, I normally love the way my boyfriend dresses. (I’m an easy lay—a simple oxford and cotton slacks gets me there every time.) However, sometimes his casual look can be triggering. Recently, he left the house wearing men’s yoga pants (an oxymoron) and those terrifying toe-shoes that look like a glove for your foot. I was like, “Is this performance art? Or is this just who you really are?” When I asked WTF were on his feet, he responded: “Amphibious footwear, bitch—they work on land or sea.”
For the whole day I was painfully aware of whether people were looking at his feet. It felt like living inside a commercial for anxiety medication. As a couple, your partner is an extension of yourself—they represent what you respect and admire in the world. And I’m sorry, but I just don’t want coffee shop randoms connecting my humanity to shoes with differentiated toes.
(Author’s note: After reading this, my boyfriend pointed out my recent trip to CVS wearing a onesie giraffe suit—a late-night Target joke purchase that has evolved into my preferred sleepwear. While in the deodorant aisle, a child yanked my tail and asked if I was dressed up for Halloween (it was July). Apparently, my boyfriend’s acceptance of my giraffe attire makes him a “better person” than me. Hmm...)
Of course, style is about more than just clothes—it encompasses our entire aesthetic existence. So if your partner wears jackets with a million unnecessary zippers, then good luck decorating your apartment. Even if you like their style, it can be a struggle. Just last week my boyfriend and I spent all Sunday arguing over whether the living room needed a tacky pink velvet chaise lounge (clearly) or this creepily heavy oak rocking chair that looks like a prop in Rosemary’s Baby. I wondered, Am I in an aesthetically abusive relationship?
But can a style clash ever be a turn-on? My friend Kaitlin, a fiery redhead with strong Twitter opinions, argues that in rare cases, the impossible may be possible.
Kaitlin met her boyfriend a few years ago, when she DM’d him about buying one of his paintings. “I was single and boy crazy,” Kaitlin told me, “so I thought every guy I met could potentially turn into a thing. But when I showed up to his studio, he was wearing pink camo pants, crocs, and ear gauges. He looked like the sort of person who likes music, you know what I mean? I immediately thought, Okay, friend zone.”
Yet, astoundingly, his personality transcended his stretched-out earlobes, and they started dating. At first, his style was like the third person in their relationship. Kaitlin told me, “He has this one T-shirt with a drawing of Snow White bent over backwards, fingering herself. When we went out, I could see people staring at his shirt and then frowning at me, as if him not wearing a suit indicated some moral failing on my part.”
But over time she found his defiant attitude contagious. “People always lie and say they don’t care what people think, but my boyfriend truly doesn’t care. I secretly admire it. Because imagine the opposite: a guy who self-consciously wears James Perse shirts and buys his jeans at Barneys.” Agreed: offensive.
Clearly, there’s a difference between having a style and being stylish. And after experiencing her boyfriend’s annoyingly personal wardrobe, Kaitlin wondered whether, tragically, she was the latter. “The way my boyfriend dresses is so specific to him. He’s so himself, and it’s extremely appealing. Like, I obviously didn’t think I’d grow up to date someone who wears joke T-shirts. That’s not my Hollywood fantasy. But whatever, he’s literally the coolest person I know—way cooler than anyone who thinks his shirts are dumb.” Essentially, confidence trumps everything.
As my rich, cunty friend from Milan once told me: “It’s wonderful to love the way someone dresses, but fashion feelings are not the same as real feelings.” How wise. If someone is worth dating, they should, as a prerequisite, transcend their pre-distressed denim. The goal is to get to the point in life where you’re comfortable enough with yourself to say, “He likes those hideous toe-shoes, and he’s who I chose.” Perhaps that is the true definition of love.
Originally Appeared on Vogue