Last month, I broke up with my boyfriend. Or, well, he broke up with me. Via text message.
On my birthday. While I was standing in the middle of the grocery store making dinner. The timing was so cruel it almost took my breath away.
Like someone opened up the handbook for How To Break Up With Someone and then tried to upstage the author with their own sadistic twists. I called my friend Emma.
Everyone has an Emma.
As soon as you find yourself in need of emergency emotional assistance, you call your Emma.
Ours had been friends since college, and she had raised two daughters through graduate school on little more than freelance gigs and sheer stubbornness. If anyone could administer emergency emotional CPR, it was her.
I spent approximately 17 minutes crying into the phone at ugly-tempo until Emma asked me a question that made me stop, mid-snort-cough, out of sheer bafflement: “What were you wearing when you met him?” The question was so unrelated to my current crisis that it took me a second to think past my rage dump enough to answer. “Um, skinny jeans? That brown jumper I like? It’s warm!” Emma paused.
And then she said, as if she had just won Jeopardy: “That’s why he asked you out.” Emma wore trackpants so low on her hips you half expected them to autumn down during our dates, and she liked her tops big enough to hide in. She was not a jumper-dessert kind of girl. Yet there she was suggesting my oversized beige muff-coat was my wingman.
I could have worn a bin liner and Emma would have found a logical reason why that sparked his interest, too. I will give her that much. But The Jumper, as we refer to it in my grief cycle, is special.
It is wide enough to fit both of my brothers. It is a loose shade of beige that scientifically cannot be worn with anything but black slacks. I have owned it for more than half of my relationship with its now-former owner.
Ifhipster chic were a person, they would wear this jumper. “This jumper,” I screeched down the phone, “is a grandpa jumper.” “That jumper is what he likes,” Emma responded aggressively. “Big jumper wearing is in.” Her delivery was so matter-of-fact I was unsure how to respond. So I dropped the phone on her foot. *** Since the breakup, I’ve been thinking a lot about what Emma said. Sure, partly it was easier to think about jumpers than process the simultaneous traumatization of having your SO dump you on your birthday.
But I’m also a fashion writer who cannot ignore a loosely valid trend-hypothesis when she sees one. Is jumper-loving objectively sexy? If so: What else isn’t sexy, but secretly is?
Are we all buying into conventional ideas about what’s date-night appropriate when we should be breaking all the rules? I started comb through relationship coach mansplainers on social media expecting to see a bunch of TED Talk slides advocating for fitted silhouettes and calculated skin exposure. But everyone I reached, from dating app relationship psychologists to NYC-based speed-dating consultants, confirmed my suspicions about big, baggy, au naturel style being the new black. “When it comes to first impressions,” says NYC-based dating coach Morgan Burke, “less is more.” “The whole oversharing-your-personality-through-your-clothes thing is actually really offputting,” confirms Maykara Chavez, a relationship expert based in California. “Wearing things that are clearly uncomfortable just to look sexy screams low confidence.” Apparently showing up to a first date trying not to look sexy is the hottest thing you can do.
The jumper just became my new power suit. Or at least, that’s what I thought until I interviewed Chicago-based relationship psychologist Dr. Maya Rodriguez and she completely dismantled everything I thought I knew about sex, clothes, and attraction. “First of all,” she laughs, “your jumper probably had nothing to do with him breaking up with you.” The jumper isn’t just good for dates, it turns out.
It’s great for breakups too. “If anything,” she continues, “that jumper probably had the opposite effect. Your jumper is the epitome of what we call ‘low-effort attractiveness.’” We may think we’re hungering after peak-hotness when we show up to a date dressed to kill, but what we’re really doing is engaging in a highly fetishized version of foreplay. Something about a low-cut shirt and high heels just screams “I want to f*ck.” “A lot of people think being ‘sexy’ means showing as much skin as possible, or wearing something very figure-hugging,” Dr.
Rodriguez tells me. “But when you dress in a way that’s too obviously aimed at being sexy, you’re not coming across as confident and secure in who you are; you’re coming across like you need someone else to find you attractive.” The ugly jumper sends an entirely different message. “When you wear something that’s deliberately unflattering, you’re signaling to potential partners that you’re comfortable with who you are and what you look like barebones,” she continues. “You’re telling them that you don’t feel like you need to put effort into looking sexy to go on a date with them. Subconsciously, that’s incredibly attractive.” She’s not the only expert singing the praises of fashion that leans more relaxed than risqué. Terrence Jackson, a dating coach who works with clients all over the United States, tells me he’s “always encouraged clients to push back against instinctive ideas of what we think will ‘turn someone on.’” “My advice has always been to showcase your authentic self on a first date,” Jackson says. “Oversized shirts, slightly-too-big-for-you jeans, even big ugly trainers sends a signal to someone that you’re not stressed about ‘performance’ when you’re with them.
The guys that trust my approach report back to me that women are more receptive, friendly, and open with them.” The numbers seem to back this up, too. When I reached out to dating app Hinge for data on supposedly “unsexy” garments that have historically performed well on profiles, I was met with a dizzying array of surprises. Conversations started, Jin Park, a trend researcher at Hinge, explains, have skyrocketed 55% around profiles featuring “oversized knits,” up 30% for women wearing ”chunky” heels and loafers instead of strappy sandals or high heels, and 21% more women are receiving replies when they forego heavy makeup in favour of “natural-looking” photos.
That final one surprised me most of all. “I think what we’re seeing,” Park explains, “is a shift in how people are thinking about dressing to appear ‘sexy.’ It used to be that showing up to a date looking like you tried really hard was the goal. Now, we’re seeing a huge increase in people opting for more comfortable clothes that send signals of ‘approach me if you want to,’ rather than ‘please fuck me.’” I even went direct to Instagram followers for some anecdotal evidence, sending out a casting call for responses to the questions: What turns you on about your partner’s style, even if it’s “not traditionally sexy?” The responses I got were so explosive my iPhone nearly caught fire. Giant mumu dresses, Birkenstocks, dad trainers, shapeless jeans, unkempt hair… the list goes on. “I love guys in clothes that give zero f*cks,” read one response. “When a dude walks around in clothes that don’t seem fashionable at all, it makes me want to take care of him.” “Guyfriend jumpers,” wrote another. “The bigger and boxier, the better.” “I love socks and trainers with dresses,” shares one of my friends. “If you can pair a cute dress with an athletic shoe and look good, I’m automatically attracted.” It’s official.
My weird jumper is the new Jordans. Or is it? Have we all been so brainwashed by generations of “sexy = thin, white woman covered in bodycon dresses” propaganda that we forget what we find hot to begin with? “What we’re really seeing,” Dr.
Rodriguez says when I ask her this question, “is a reaction to social media culture and the relentless pressure that puts on people to look a certain way all the time. No one wants to date someone who’s only hot when they’re wearing their ‘nicest’ clothes.” This should come as no surprise to anyone who spends any amount of time talking to stylish people about what they wear. The most stylish among us have always known that clothes don’t get more flattering than clothes that make you feel good.
They may not look conventionally sexy, but they exude sex appeal because they project confidence, individuality, and creative vision. If you talk to anyone who’s serious about their style, they’ll tell you the last thing you want to wear on a date is a dress that literally molds itself to your body. Of course, I had to verify this outside the circles of people who live and breathe style.
So I promptly coordinated four dates with four separate men using the exact same criteria: Same dating app. Same level of face-decor (10 percent makeup for those playing along at home). Same breakfast and lunch dates at black coffee cafes.
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The only difference? My outfit game. Date #1 operated as the control.
I wore what I instinctually felt most comfortable in: a body-skimming wrap dress that highlighted my waist, low heels, feminine jewellery, hair brushed and curled. Something sexy. The date itself was…okay.
We talked about work, where we grew up, our hobbies. It was pleasant. But by the end of our date, I wasn’t excited to see him again, and he wasn’t excited to see me.
We left wishing each other well, made no plans to meet again. Date #2 was The Jumper. Yep, I wore that gremlin down to Hoyt Street Cafe and talked boys with it.
This time, things went far differently. Maybe it was the jumper. Maybe we just hit it off.
But within minutes of meeting he noted that my jumper was “really cozy” (not a compliment, I know, but hey….). We talked for two and a half hours. When we left the coffee shop he asked me on another date.
Date #3 was, shall we say, extra extra extra ugly. We’re talking big-boyjeans held up by an oversized cloth belt, Birkenstocks (dontjudge! ), and a boxy blazer that I’m 90% sure was stolen from my dad’s closet. It was not sexy.
But holy hell did it work. Much like date #2, the connection was there from moment one. He asked thoughtful questions and actually listened when I answered.
We talked about everything from favourite books to weird family anecdotes. By the end of the date, we had made concrete plans to get dinner together the following week. Possibly spurred by Date #3’s success, I went all out for Date #4.
Beanie hat, leggings tucked into rain boots, oversized blazer…you name it, I wore it. If I ran into anyone from my wardrobe carbon-copy Date #1, I seriously doubt they would have recognised me. Best.
Date. Ever. We not only had a fantastic conversation, but there was zero pressure.
Zero. I actually enjoyed talking to him without feeling tense about whether he thought my shirt was too low or my heels were too high. We spent the day getting coffee, then went to a food truck together for tacos, then sat in the park and talked until it got dark.
It was perfect. So what’s the takeaway here? Have I unlocked the secret to dating by dumbing down my outfit aesthetic?
I can’t say for certain that showing up to your date underdressed is the answer to all your relationship woes. But I will say that after four very distinctly styled outings with four very differently guys, something stood out to me about every single date where I wore something eschewed clothes traditionally coded as “sexy.” “When you wear something that you feel comfortable and confident in,” says dating coach Jackson, “you’re able to be present in the moment a lot more. You don’t have to spend half the night worrying about whether your shirt is sticking to your backs of your thighs, or if your heels are going to rip a hole in your dress when you sit down.” Dating expert Dr.
Rodriguez agrees: “Wearing something that signals you’re ‘trying’ to look sexy is actually the least sexy thing you can do. You’re putting up a wall between you and potential partners that says ‘I’m trying too hard.’ When you wear something that takes the sexual element out of the equation, you’re telling someone: ‘I want to show you who I really am.’” And that, I think, is the crux of what’s so sexy about dressing “unsexy”: Putting effort into not looking like you’re trying too hard. “That confidence you exude when you’re not worried about beingsexy” Dr.
Rodriguez continues, “is magnetic.
There’s a reason why some of the most stylish women in fashion don’t give two cents what society tells them is flattering or not.
When you stop caring about what other people think of how you dress, you open yourself up to being absolutely anything.” Including, but not limited to: dating success. Now, to be clear: dressing “unsexy” is not an invitation to lazily throw on whatever trousers paired with whatever shirt you grab from your closet without showering.
There is a difference between looking “deliberately unkempt” and looking homeless. “The biggest mistake women make when they think they need to dress ‘unsexy’ for dates is that they still try to hard,” says Chavez. “If you don’t love that baggy jumper, or those giant baggy jeans, wear something else that you feel confident in. Trust me, he will notice.” So yes, while your favourite bodycon dress isn’t “over” per se, there’s nothing stopping you from mixing up how you dress to impress. Try showing up to your next first date in that baggy jumper you love, or a pair of jeans that don’t quite cinch at the waist.
Maybe even rock those headphones as a top like the stylish Parisian you are. Trust me, your dates will thank you. And if they don’t?
Well, there’s plenty more jerks to dump in that gigantic jumper of yours. Speaking of which: jumper boyfriend and I had lunch together recently. He saw me from across the cafe and laughed. “I always thought that jumper looked good on you,” he said with a smile.
Kids these days.
