Last month, I got dumped. via text. on my birthday. while i was in the middle of buying ingredients to cook this person dinner.
As one does in these situations, I immediately called my friend Emma for emergency emotional triage. After listening to me ugly cry for approximately 17 minutes, she said something that temporarily stopped my crying through pure confusion: “what were you wearing when you met him?”
This seemed like an odd question, considering the circumstances. “uh, i was wearing jeans and that oversized beige cardigan i bought at the vintage store? the big, chunky one that looks like it belongs to someone’s grandfather? why?”
there was a long pause before emma said, “oh yeah. that’s probably why he asked you out in the first place. trust me.”
i was confused. the cardigan in question is big, shapeless and the colour of oatmeal. it has large pockets capable of holding an entire convenience store’s worth of snacks. it is clearly unattractive.
if the sweater were a person, it would be a middle school math teacher named gerald who collects commemorative spoons and goes to bed at 8:30 pm.
“emma, what are you talking about? that cardigan is basically a form of birth control,” i replied.
no, no, it’s a thing,” she said. “big, oversized cardigans are actually very sexy right now. i read an article where dating coaches were saying it’s like the new sexy. something about being cozy and approachable.”
i was skeptical, at the least. however, emma’s comment stuck with me because it was easier to think about sweaters than to process my birthday dumping. and since i am a fashion writer who is pathologically unable to leave any style-related claim unexplored, i decided to explore this further.
is the unattractive sweater truly the new sexy? and more generally, are there other “unattractive” fashion choices that are indeed attractive to potential partners? is everything i know about how to dress for a first date totally wrong?
to begin exploring this, i contacted a few dating coaches/relationship experts and expected to receive the typical suggestions regarding how to emphasize the silhouette of one’s body through clothing, as well as strategically expose skin. instead, i received an ear full about the unexpectedly alluring quality of deliberately unattractive wardrobe choices.
“the oversized cardigan is actually a perfect example of what we refer to as ‘approachable attractiveness’,” explains dr. maya rodriguez, a relationship psychologist who consults with a few dating apps on user behavior. “it signals that you are comfortable with yourself, and that you don’t put forth an obvious amount of effort, which paradoxically translates to confidence—and that is one of the most attractive qualities universally.”
apparently, my dumpage had absolutely nothing to do with my cardigan. if anything, the sweater was likely the reason he asked me out in the first place. the betrayal runs deep!
but dr. rodriguez was not the only expert raving about deliberately unsexifying style. dating coach terrence jackson, who works with clients in nyc and los angeles, has been suggesting to his clients to include what he refers to as “comfort signaling” in their first date wardrobe.
“i’ve been telling my clients to steer clear of the obvious ‘try to be sexy’ options for years,” jackson explained. “particularly for women dating men, there is something about an oversized sweater, a pair of worn-in jeans, even those clunky “ugly” shoes—that provide an immediate sense of authenticity and approachability. my clients who choose this option consistently report stronger connections with their dates.”
the numbers support this as well. dating app hinge recently analyzed photos in the top 1000 most successful profiles (by measure of matches and conversations that resulted in sharing phone numbers) and found that casual, slightly sloppy looks greatly outperform conventionally appealing first-date attire.
“profiles featuring oversized knitwear had 30 percent more positive interactions than those featuring more typically ‘sexy’ clothing,” reports jin park, a trend analyst at the company. “we’ve also seen a 45 percent increase in positive reactions to photos featuring chunky loafers, flat shoes, minimal makeup, and other perceived “unsexy” style options.”
this trend is not exclusive to heteronormative dating. “across all gender identities and sexual orientations, we are seeing a shift towards the value of authenticity over the typical ‘sexy’ ideal,” park continued. “the time of dressing like you are trying to be as attractive as possible is basically over.”
to gain a more personal perspective, i solicited feedback from my instagram followers. i asked them to share examples of the “unsexy” things they find attractive in a partner’s style. the responses poured in so quickly that my phone almost crashed.
“men with those massive wire-framed glasses that look like they were issued by the soviet government in 1983,” responded one woman. “something about a man who does not care whether his glasses are ‘cool’ is super attractive to me.”
“somewhat too short pants on women,” responded a man. “not intentionally cropped, but like they’ve had them for years, and they shrunk a bit in the washer. it’s cute.”
“work boots that are actually scratched from work,” commented another. “not the polished construction boots people wear to brunch, but the ones that demonstrate someone actually constructs things.”
and yes, many, many people specifically mentioned oversized, shapeless cardigans as attractive. emma, it appears, was correct.
what is happening here? have we simply decided that “sexy” is not sexy anymore? and if so, what does that mean for how we dress when we attempt to attract a partner?
according to dr. rodriguez, this change represents larger cultural shifts in how we view attraction and relationships. “after years of highly filtered, perfectly curated social media displays of oneself, there is a growing disdain for obvious effort,” she explains. “showing up in something deliberately unsexy demonstrates that you are not attempting to seduce anyone with your clothing—you are inviting them to meet the real you.”
this mirrors something i’ve observed in the world of fashion as well. the most stylish people will often wear items that defy common assumptions about what constitutes “flattering” or “sexy”. the coolest person at any fashion event is rarely the individual wearing a fitted dress and high-heeled shoes—it is usually someone wearing a visually interesting combination of items that emphasizes comfort and personality rather than the traditional definition of sex appeal.
however, i wished to test this theory beyond expert opinion and anecdotal evidence. therefore, i devised a highly unscientific experiment. i would attend a series of first dates in deliberately unattractive outfits and observe the results. for comparison purposes, i utilized the same dating app, wore the same minimal makeup, and selected similar casual coffee shops. the only difference was the level of conventional sexiness in my outfit.
date #1: the control
for my control, i wore what would be traditionally regarded as a “cute” first date outfit: a fitted wrap dress that accentuates the waist, low heels, dainty jewelry, and hair that is down and styled. the type of outfit that women’s magazines have been recommending for first dates since about the dawn of time.
the date itself was okay—we had some decent conversation—but by the end of it, i wasn’t really interested, nor was he. we danced the awkward “we should do this again sometime” dance with no concrete plans. there was no second date.
date #2: the unsexy cardigan
for the second date, i wore the Cardigan—the exact same oatmeal-colored monstrosity that spawned this research—together with basic jeans, a plain white t-shirt, and flat ankle boots. my hair was tied back in a low ponytail. i wore the same light amount of makeup as date #1.
this date went surprisingly well. the conversation flowed naturally, and my date even brought up my sweater, stating it looked “really cozy” (which, let me tell you, was no way intended as a backhanded compliment). we spoke for nearly three hours. he requested a second date prior to us leaving the coffee shop, and there was a genuine sense of familiarity to our parting that was absent in date #1.
date #3: deliberately unflattering
for my third experiment, i took the idea of unsexy to its extreme: oversized vintage men’s pants secured by a canvas belt, clunky-looking orthopedic-style loafers, and a boxy button-down shirt. none of this outfit “flattered” my body in the conventional manner. i looked as though i was auditioning for a local theatre production of “annie hall: the later years.”
once again, the result was a successful connection. my date seemed to be genuinely interested in becoming better acquainted with me, asked thoughtful questions, and did not engage in the awful practice of men’s eyes drifting downward throughout the course of the conversation. we discussed books, shared family stories, and once again, planned a second meeting.
date #4: peak unsexy
for my last date, i channelled what i believe to be “peak comfort signaling”: baggy jeans, a cardigan even larger than the one from date #2 (one borrowed from my brother), scuffed shoes, messy bun, and minimalist jewelry. i looked like i might be ready to paint a wall or assist in moving furniture.
this turned out to be the best date of the series. not only did we have a strong connection, but there was also an obvious absence of the standard first-date performance anxiety on both parts. we walked around the neighborhood post-coffee, obtained tacos from a food truck, and sat in a park discussing topics until nightfall. the connection felt natural and effortless from the onset.
so, what did i take away from this experiment? while i cannot state unequivocally that deliberately unattractive clothing is the key to successful dating (n = 4), it appeared to be true.
“that makes sense when you think about it,” states dating coach jackson. “when you are not concerned with presenting a ‘sexy’ image—you are constantly checking if you are exposing too much or too little, adjusting straps or hems, etc.—you are present for the date. that presence is infinitely more attractive than any outfit could possibly be.”
dr. rodriguez provides additional insight: “conventionally ‘sexy’ clothing often serves as a barrier to forming genuine connections because it is inherently performative. when you are dressed in something that is comfortable and authentic to your everyday self, you are effectively stating ‘this is who i really am; not who i am pretending to be for your sake.’ that authenticity is attractive.”
there is also a certain degree of confidence involved in presenting oneself in deliberately unattractive attire. “wearing an item that society deems to be non-traditionally attractive requires a degree of confidence that is much sexier than adhering to societal standards,” states park. “it communicates that you are dressing for yourself, not for the approval of others.”
as previously stated, i have observed this principle within the realm of fashion for many years. the most respected style icons (e.g. phoebe philo, jenna lyons, raf simons)—all of whom have expressed a deliberate preference for deliberately unattractive elements: oversized proportions, practical footwear, comfort over conventional flattery—also express a style that is deemed fashionable in fashion circles and authentic in dating circles.
however, it is necessary to note that the attractiveness of deliberately unattractive clothing is not about hiding yourself or adopting slovenliness. it is about wearing things that emphasize comfort and authenticity over conventional sex appeal. the cardigan needs to be a cardigan that you love and feels good to wear—not just any large cardigan.
so, where does this leave traditional first-date dressing advice? is the little black dress dead? should we all begin attending romantic dinners in orthopedic shoes and loose-fitting garments?
for me, this exploration has been surprisingly freeing. as a fashion writer, i have spent many years contemplating how to fashionably display my body in a flattering manner, only to realise that pursuing flattery may not be the most effective means of connecting with others—not just in terms of style, but in terms of genuine connection.
currently, my go-to first date outfit consists of jeans, shoes i can actually walk in, and yes, frequently the enormous oatmeal cardigan. i have had more second dates in the last month than in the previous six months.
