The Burden of Having an Unfashionable Boyfriend

By Isla Mitchell ‘26

Graphic by Isla Mitchell

There’s a long history of asymmetry in the coupling of two people, in which one partner surpasses the other in terms of style. Think Kim and Kanye, Gisele and Tom Brady, and most famously, Justin and Hailey Bieber. These are just a few examples of an age-old archetype that plagues not only pop culture but also our daily lives. I am sure that you, too, have borne witness to this unfortunate asymmetry. It happens so frequently it almost appears to be a natural phenomenon. It’s a condition of society that we have yet to cure, and sadly, it appears that I have fallen victim to it. Why does my boyfriend dress like shit?

I take my condition quite seriously—although I remain unmedicated. While I am often described as aloof and perhaps rarely understood to be self-aware, one thing that I am dreadfully aware of is ornament—I care about how I dress. My closet is an annex of identity—the conglomeration of years of culturally informed purchases, stolen inspiration from my friends, and thrift store trips with my mother. My credit card statement would say I am overly involved with aesthetics and need to get off Depop. So, why does my boyfriend dress like shit?

Throughout my childhood, I had the privilege of being surrounded by men with personal style—artistic, city-adjacent folk who were perhaps too involved with the fantasy of individuality. My father and my brother were both art history majors at Vassar. This means that they graduated with an extraordinary amount of pretension but also knew how to dress in an interesting fashion. My father curls his mustache. My brother rocked Marimekko in the ninth grade. So, why does my boyfriend dress like shit?

I have not contained my concern. Evocations of my distress have taken the form of subtle remarks—“Are you sure about that?” “What if you change your shirt?” “Do you even own a cashmere sweater?” Upon reflection, I say these things rather honestly and consistently, in hopes that these comments will inspire some form of self-reflection in the future. Perhaps my projections will stick. Suddenly, he will become some fashion icon under the influence of my well-informed, well-intentioned microaggressions. In the meantime, the question remains, why does my boyfriend dress like shit?

Recently, I brought up my distress to him. I said, “Babe, why do you dress like shit?” He was offended—the truth is also a burden that’s hard to bear. However, he offered what may seem like a satisfactory solution: “I will buy anything you tell me to buy; I will wear what you tell me to wear.”

Some may think this is the ideal situation. However, discontent is an utterly human condition. I ask myself: why should I have to compensate for his lack of creativity? I am already the creative director of my life; why should I be the creative director of his as well? And if I do agree to this creative endeavor—perhaps I adorn him in a pair of jeans that fit, a non-polyester T-shirt, and a cashmere sweater, if he’s so lucky—what happens if we break up? He becomes my horcrux—a projection of me, strutting around in my style. He may be the walking image of my personal drip. That is a new kind of burden.

Undoubtedly, I am being too harsh. My vanity escapes me. Perhaps I take myself too seriously. Perhaps he offers some sort of insight into a brighter reality—one in which man is not so encumbered by self-perception. If I am not willing to break up with my boyfriend after seeing him in tapered pants, there must be some sort of reconciliation. Perhaps the question is not why does my boyfriend dress like shit, but rather, is it cool that my boyfriend dresses like shit? Is there sophistication in those unaffected? Is there a bespoke aesthetic to those naturally unfashionable?

No. The Middlebury logo tee can simply be unimpressive. A golf shirt stands as the antithesis of my libido. I do not have to concede to the idea that it is somehow fashionable to be unfashionable. Ultimately, my boyfriend dresses like shit, and it’s simply a burden I have to bear. If I handle it with grace, perhaps that will only improve my own style. I bought him a cashmere sweater; we’ll see if things improve from there. If you have any other