I Dressed Like A Hipster to See If More Guys Would Hit On Me (And They Did)

I went from crop tops to painters' smocks. Guess which look got me into a VIP afterparty?
Publish date:
December 15, 2015
clothes, fashion, hipsters, androgynous style, Social Experiment

Two years ago, when I moved to Vancouver, noticed early on that there was a very specific look in my new city and among my new friends. Just like high schools all have different in crowds, every city has a look that has denotes its particular coolness.

The boys I have crushes on — a diverse range of men who could all, nonetheless, be described as “hipsters" — all seem to be dating the same type of "cool girl." These girls dress, more or less, in ill-fitting, androgynous clothes. They wear flatform sneakers and fanny packs slung subversively across their chests. Invariably they sport a topknot and no make-up.

These girls are beautiful and achingly cool.

I don't look anything like them. I am a devotee of tight clothes, short skirts, and platform sandals. I like my accents to be shiny, glittery, fluffy, and furry and I like my purses impractically tiny. My look has been described as “slutty and well-read.”

Having a personal style that's more or less the antithesis of what all the cool kids are wearing, left me feeling awkward and, sometimes, a little judged. But much as I was feeling the shade when I rolled up to a gallery opening with acrylic nails and a tube top, I was guilty of throwing it right back. I'll admit it — I judged shapeless, hip clothes and the girls who wore them.

“What do you have against cleavage?” I silently interrogated them. Translation: What do you have against ME?

Knowing how lame and hypocritical this was, I decided that I should walk a mile in someone’s Stan Smiths before judging them. I would go out in disguise — dressed like the girls I have such complicated crushes on.

I’m going to level with you. I had an ulterior motive. The majority of the girls I would be emulating were dating foxy boys — the types of guys I stalked on Instagram and hoped I would run into at brunch. I thought the cools girls might be onto something. Maybe their brand of “I’m not trying” appeal was the most effective when it came to catching the attention of hipster boys.

To assist me in this social experiment, I enlisted the help of my two roommates. One is a shop girl at the hippest boutique in town — she is also the face of their Instagram, something that requires her to stand in front of a white background pouting and wearing burlap tunics. The second is an accomplished photographer. One would style me in the aesthetic of her hip employers and one would document the transformation.

That weekend, all my girlfriends came over to help me dress up. I put on flatform sneakers, mom jeans, and a buttoned up blouse. Everyone booed when I walked in the kitchen.

“It’s too cute!”

“You tucked in your shirt! That’s against the rules!”

“I’d actually wear that!”

My roommate took control of the situation. Deciding that I was, “literally incapable of doing this properly," she confiscated my hoop earrings and unearthed a white broad-weave garment from her closet. It looked like a painter’s smock, or an undone straight jacket. “I bought it in Korea,” she said, “and before you judge me, I only wear it with tiny shorts.”

The painting smock was perfect. It totally looked like I was en route home from my ceramics studio, or like I was a 19th-century monastic painter.

When we got to the venue, I wanted to hide. But, in the name of undercover journalism, I bought a drink and lurked near the side of the stage. Every time I worked up the courage to talk to a guy, I’d glance down at my sweaty PBR and drooping, saggy jeans and scuttle off to the stage for more pointed lurking.

The next weekend I attended another concert at a huge venue I'd never been to before, wearing the same getup. Again, no makeup and the infamous half topknot. I resolved to be more bold this time around and decided that the V.I.P section was the perfect petri dish for my experiment.

A single bouncer guarded the section (meaning there was one of him, not a reference to his relationship status). He let me in after exactly four seconds of conversation that went like this.

Me: “Hi, what’s going on there?”

Single Bouncer: “That’s the V.I.P. You should be in there.”

Easy. And all while dressed in a smock.

I grabbed my friend from the bathroom line up and we slipped past the rope. Before the set was over, I had one free drink and an invitation to an after party at a nearby strip club. I shared a taxi to the club with an absurdly handsome hairstylist who had the most magnificent man bun I'd ever seen. (Honestly, I was transfixed by how perfect his hair was.)

The strip club featured naked women (obviously) and free tequila (slightly less obvious). Man bun was gaming like crazy. I’m not saying that he didn’t have beer goggles, but were IN A STRIP CLUB, one that was populated by as many girl patrons as girl employees. Given the circumstances, I had to conclude that he was sincerely into my look, which he described as “sexy as fuck.”


But also, not. What the whole experience made me think about was the effort-to-confidence ratio that is at the center of the way I dress.

The more I try, the better I feel. When I wake up I put on a costume. In a way, I’m undercover all the time. The girls I was so obsessed with do the same thing; they just choose a different set of disguises than me. So what if they want to look like they belong to a certain tribe? So do I, so do most of us.

I think the idea that hip girls are popular with foxy hip boys because of the way they dress was a total miscalculation on my part. What I do think is that these girls have a really irresistible kind of confidence. If you feel confident in a painters smock and 400-dollar flatform sneakers, that’s not any different to feeling good in a little dress and your priciest heels. The objective to getting dressed should be to wear the uniform that makes you feel like your best self.

Experimenting with another look didn’t make me want to abandon the way I normally dress. I still love my wardrobe and my way of doing things. Since I went undercover, though, I realized I don’t need to look any one way to have fun. A good mood and a willingness to go outside my comfort zone is the most flattering look I’ve ever tried, and the best part is how well it goes with any style.