It’s Complicated: My Relationship with the “Boyfriend” Look

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Photographs courtesy of Lindsay Wang

I live in my “boyfriend” jeans. They sag on my hips. They don’t accentuate any curves I might have hiding away somewhere. They aren’t traditionally flattering, yet they remain one of my most worn articles of clothing.

My love for “boyfriend” style clothes doesn’t just stop at jeans. I also regularly sport boxy tee shirts and oversized button downs that were purchased in the men’s section. I even have an entire drawer dedicated to my “grandpa sweaters” with sleeves that hang well past my fingertips.

When I first wandered into the menswear section, I felt embarrassed and uncomfortable. I found myself keeping my eyes down to avoid eye contact with anyone as I tentatively flipped through racks of crisp dress shirts and bro tanks. I was self-consciously found myself thinking that maybe I don’t belong in this section. I particularly remember one interaction from a year ago that I had at Cotton On while shopping for a new flannel in the men’s department.

“Looking for something for your boyfriend?” a stylish male sales associate asked me.

“Um, no thanks. I’m actually shopping for myself,” I replied.


“Oh…” he paused, looking me up and down. “All right, well let me know if you need anything. Our ladies’ section is on the right side of the store if you want to find something with a better fit.”


I mumbled a quick thank you and scurried to the back corner where I briefly examined a polka dotted fit and flare dress before promptly hanging it back up, well aware that I didn’t even need to try it on to know that I wasn’t going to purchase it.

Even though I identify as female and use she/her pronouns, I don’t feel like I embody society’s ideal woman. I don’t have the “womanly” curves that most of my female friends do, not do I have one of the bombshell bodies plastered on glamorous billboards. I grew up struggling with fashion magazines labeling my body type as “boyish.” For years, I found myself overcompensating for my figure by stocking my closet with dresses and blouses in lace and chiffon. Everything was delicate and dainty in either a soft pastel or floral print—or both. Even though I thought that these articles of clothing were pretty, I eventually realized that they didn’t truly represent my personality.


After this epiphany, I slowly began to curate new clothing pieces that I felt more comfortable in. I started with a few big tank tops from the men’s clearance section, and then advanced to buying myself oversized cardigans. My real turning point however, was when I was finally comfortable enough to graduate from thigh-constricting skinny jeans to my Holy Grail item: my beloved “boyfriend” jeans.




















It was indescribably liberating to transition to loose cut clothing. I no longer had to spend ten minutes pouring myself into a tight denim second skin and I stopped worrying about whether or not my body looked like someone else’s.

However, as much as I love the freedom of wearing loose jeans, I struggle with the term “boyfriend” cut. This title suggests that I’m wearing men’s clothes as a badge of honor to tell the world that I’m in a relationship with a male who lets me borrow his pants after spending the night. It bothers me that bigger, looser clothes have to be marketed as being “boyfriend” cut in order to belong in the women’s section. This implies that only men are allowed to wear baggier clothes and the only time women can choose this comfier alternative is when a man she’s in a relationship with gives her his own clothing.


Additionally, I have found that lots of “boyfriend” cut clothing often does not resemble anything that is actually made for men. “Boyfriend” button-downs are nipped at the waist to create a

slimming effect. “Boyfriend” tees are made of thinner material to accentuate curves. I try to avoid these pieces because I feel like they defeat the purpose of wearing menswear-inspired clothing by purposefully highlighting traditional feminine body features, despite the “boyfriend” label. Alternatively, slim cut clothing items for men are not advertised as “girlfriend” cut; they’re just tighter fitting clothing for men. Women’s clothing is not granted the same fluidity.

I don’t wear men’s clothing to pretend I have a boyfriend or keep up with the latest trends. I choose to rock androgynous clothing because it has helped me embrace my body in a way that makes me feel more secure as a woman. I don’t need to conform to ideal dress standards of femininity to feel comfortable in my own skin. I can put together an entire look made up of menswear pieces that I feel incredible in. This isn’t because I’m trying to hide my body behind boxy sweatshirts or reject my femininity by never wearing skirts again. Rather, I’m embracing the fact that I don’t have to look a certain way to be a confident woman.


So if you see me shopping in the men’s section, you can assume that yes, I am shopping for a relationship; I’m shopping for my happy, healthy relationship with myself.