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I have B or C cup breasts, depending on how much ice cream I've been eating. I like them. They are great. They are fine. I can just about fit one in each hand. And I hate strapping them into any kind of bra.

It's generally accepted that smaller-chested women don't have to wear bras. Medium-chested women (a most sexy term, "medium-chested"), among whom I suppose I count, can go either way. I don't need one for support — unless I'm running, my breasts don't pain me — and it's debatable whether I need one for "decency" or to avoid vulgarity. Certainly I've been out in the world and seen a woman not wearing a bra and thought: "That woman is not wearing a bra. She should wear a bra." But why? So my eyes won't be drawn to her nipples and the movement of her breasts as she walks? (Or perhaps, so the eyes of a companion won't be drawn to her nipples and the movement of her breasts as she walks?)

My body nearly always looks better with a bra on it (the exception to this is if I'm naked, in which case the bra is a joke — get out of here). Sometimes what an outfit really needs is an uncomfortable undergarment to push one's breasts up and together. A bra makes me stand up a little bit taller. It gives me some cleavage. With my breasts looking bigger, my waist and stomach look thinner. My clothes fit better. It's a better look. I know this. And yet: Whenever I can swing it, I go without. And I still feel a small, defiant thrill at it.

In high school, I incorporated braless-ness into my definition of feminism (Feminism, n.: believing that women can do whatever they want, and also, not wearing a bra). Down with the patriarchy and societal projections of beauty! The kind of person that I wanted to be was the kind of person who didn't wear a bra, or wear makeup except for zit-covering purposes, or spend any time picking out clothes or thinking about my appearance. I wanted to be effortless and cool. Instead, I was a teenager who spent hours putting together outfits meant to looks as if I'd just rolled out of bed. Part of that look meant no bra.

My mom has always been staunch advocate of undergarments, though she is mostly subtle in her assessments. She'll ask: "Are you wearing a bra?" when I quite obviously am not wearing a bra. When I moved back to Virginia last year from Portland, where I was almost always braless, my mother said: "I don't know how they do on the West Coast, but here on the East Coast, women wear bras." I told this story to my friend Megan with a laugh and she just looked at me and shrugged with her face. Later, while reading Tina Fey's book, she would text me this passage: "Wear a bra! You'll never regret it."

Finally, last year, I had a proper bra fitting in a department store. I had just started a new job, and while "brassiere" wasn't listed in the dress code, it was not a tits-flying-free kind of place.

The woman who fit me was younger than I am. Beautiful, hip, thin. Huge breasts accentuated by a great bra (I assume) and a deep-V tee. I stood in the dressing room in a t-shirt, my own breasts neither huge or accentuated, but just … there. "Um, I'm not wearing a bra," I said.

"I know," she said. "That's why you're here."

"So should I just take my shirt off?" I didn't want to offend her.

"I stare at boobs all day."

I took off my shirt. She wrapped her tape around my chest, and then left the room. I stood there, topless. She came back with two horrific vintage looking things. See-through mesh, heavy underwire, wide elastic straps, reinforced stitching. I put one on, and immediately hated it. It was the most uncomfortable thing. She shortened the straps, making it more uncomfortable. I made a face, and she said: "This is how it's supposed to fit."

"It's awful," I said.

"It should make you stand up straighter," she said.

I looked in the mirror, turned a bit. I was standing up straight, yes. But the too-tight, see-through bra had done other things to my body, too. There were seams and fabric everywhere and tugging and pinching, turning my once smooth back into something more reminiscent of a chicken carcass wound tightly with twine. "Is it supposed to be this uncomfortable?" I asked.

"Yes," she said. "You know it fits because the fabric in the middle is flush against your skin." And so it was, two inches of fabric, separating each breast into a separate pointy thing. "This is not your sexy times bra." This was obvious. "But it looks great under clothes."

I put my T-shirt back on over it. I did look better. "Does this really look better?" I asked, cupping my now-pointy breasts. They no longer fit in my hands. The woman just raised her eyebrows. This, apparently, was the way. I tried on a few others, and bought two $50 ones, both black, both uncomfortable. I did not wear a bra out of the store.

I'm wearing one today. My breasts look great. But at what cost? ($50, some mild discomfort, and a tinge of remorse at conceding to the status quo.)

Logan Sachon co-runs The Billfold.