mom hasn’t called, but I’m giving my roommate a makeover

Cole Habersham
5 min readJan 4, 2021

It is 12:37am eastern standard as I write this, overwhelmed, tantalized with excitement replaying the most provocative proposition uttered by my roommate on New Years Day: I’d love your help upgrading my wardrobe, he said completely sober, completely serious, completely aware just how much I love dressing and change and a well thought out ensemble.

I’m wet just thinking about this project. This is my Olympics.

My earliest memory with clothing dates back to the summer of 2003. Subject to the myth that a school year cannot commence without first securing new clothes, I asked my dad to take me shopping. We toured Foot Locker, Macy’s, and JC Penny — my unfortunate retailer trifecta that yielded an even more unfortunate first day look: a velour Jordan tracksuit with red piping, and G-Unit sneakers. I was so proud of that look for its connection to basketball culture (though I couldn’t play), how it mirrored what I saw on my black, male classmates (though I couldn’t call them friends), and its indirect endorsement by rap group G-Unit (though I couldn’t name a single song).

That first day of school, while I thought I was eating my fit up, my classmates lit me up. I couldn’t understand why. Was it the velour, or how much (and how suddenly) it departed from my usual jeans and t-shirt?

What I appreciate most about style is the opportunity it affords you to tell others a little something about yourself before you’re able to through words. My tracksuit screamed, quite desperately: accept me. And because kids are sometimes unkind, they did not.

It wasn’t until I started working at Zumiez in 2011 that my relationship with clothing changed. It became a tool to reflect the brands that employed me, that I — not having much of an identity of my own — extended into my everyday life. Though I couldn’t skateboard and had little interest in doing so, I dressed in OBEY hoodies, Vans sneakers, and unfortunate Neff beanies until I took up a job at the finest of Suburban ateliers: J.Crew; partly because the shop was a little closer to home, the clothes were a little closer to the me I was still discovering, and the pay was a little — just two dollars — higher.

In my sit-down interview with the J.Crew manager who would one day tell me to call her Princess Di (I could and would not), I said I believe in the transformative power of clothing. The thought formed quite naturally. The images I saw in J.Crew style guides, of attractive men with coiffed hair and tailored topcoats, flanked by attractive women with coiffed hair and tailored topcoats — there are some things you don’t realize you want until you see it. Track suits will always be a stretch too far for me, but a blazer is home.

It’s at that store in New Jersey where I learned to roll the perfect sleeve and expertly tuck a sweater.

It’s at another location in Manhattan where I learned how a suit comes together, the importance of tapering your pants to your leg, just how much white people love Pellegrino, and most importantly, the universal differentiators between the well-dressed straight man, well-dressed straight man looking to explore, and ordinarily, but well-dressed gay man. It has nothing to do with their clothes, really, but the degree at which their eye meets yours, and just how wide they leave the dressing room curtain open when you return to deliver their waffle henley (stories for another day).

I’ve carried these learnings — both on style and sexuality — into adulthood, finding a personal point of view on dressing that makes me feel strong and smart, by way of textured blazers, and feminine, by way of…a few things. A sheer bodysuit under said blazer, tucked into boxy Wallace & Barnes denim. Or a lightweight, light pink cashmere sweater hiked gently above my navel. My style isn’t revolutionary, but it accurately reflects who I am that day. And because one of the supremely special aspects of New York — the varied styles — I feel one of one when I step out.

The freedom to know what I wanted to wear and follow through with wearing it is one I took for granted. I long thought immodest dressing was a sin, and the very classification of immodesty didn’t leave much room for exploration. My hometown congregation taught slim pants, loud patterns, trendy styles, anything that brought undue attention to oneself was considered immodest. I was bridled with unwritten rules and expectations; classic bow ties being appropriate for Sunday service and other spiritual occasions, for example, but diamond-tip bow ties being a touch too modern. I rarely challenged these standards, but as my education at J.Crew continued, my interest in experimenting with clothing grew. In learning to style other men well, I realized I’d been buying ill-fitting clothing my entire life to adhere to a scripture I didn’t think needed to be interpreted so strictly.

Christ did not expect me to wear a 40L when I was really a 36R. A slight break in my pants would not disrupt the heavens.

The congregations in New York seemed to be on the same tip. So when I moved to Harlem in 2016 and joined a new Manhattan congregation in Chelsea, I traded up: from Men’s Warehouse to Ludlow, single to double vent, square to narrow cap-toe, becoming a version of the men I styled, and (would soon discover) found quite attractive. And then the magic happened. As I improved my dress (and by extension, confidence) I found I became attractive to them, as suggested by the severity of their eye contact, and communicated very clearly at times by a propped member in their pants I’d notice as I knelt at their foot pinning a taper and talking about the weather outside.

The inherent dynamic of these service-based romantic interactions at J.Crew has, I’m sure, contributed to toxic expectations I’ve formed concerning attraction and relationships. I’ve asked myself why puffer vest-wearing white men, settled into their 30s, often unbeknownst to me, attached, seem to be my unfortunate sweet spot. Well, you never really do get over your first.

Despite this introduction to a lesser form of what the prolific Jeremy O. Harris has named Slave Play, I owe J.Crew a small debt for providing setting and means for my first exchanges with men I found attractive, and more importantly, sparking my love of clothing. I experience that transformative power I spoke to seven years ago daily when I dress for a Foodtown run, first date, New Years Eve, or lowkiki* with my Vagabonds. It is with immense pleasure and honor that I look to bestow that power on my straight roommate, Lincoln Log.

I take this responsibility quite seriously. Mood boards are in the works. Research is currently underway. TBD if LL will be open to documenting this exciting journey, but some magic works best in the dark.

*a lowkey kiki. how brilliant is Ballet Boy?

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