Could You Date Someone With Terrible Fashion Sense?

Because we met at work, I had no idea what atrocities were waiting in my boyfriend's casual wardrobe. Think "your dad on vacation in Florida in 1989."

Feb 11, 2013 at 12:00pm | Leave a comment

Jeff and I were out to breakfast at Tallyrand in Burbank, like the old people we are on the inside, when he asked me what I was writing about this week. I told him I was working on a thing about dating dudes with no fashion sense, and he immediately looked worried and said, “Please don’t mention my [REDACTED] shirt.”

“Don’t worry," I promised, "I won’t tell the entire internet about your [REDACTED] shirt." 

So while I can’t tell you specifically what kind of shirt my boyfriend is super embarrassed to have ever owned, I can tell you that I have photographic proof that he once wore a [REDACTED] t-shirt, unironically, in the 90s, long before people started wearing them ironically like, three years ago.

Let’s just say if I’d met him in 1997, when I was 21 (and cared more about appearances and "coolness" than I do now) and he had been wearing that [REDACTED] shirt, I most definitely would not have dated him.

And in fact, when I first met Jeff, it was at work, so I only ever saw him in his work clothes. He is the kind of man who looks really, really good in a button-down shirt and dress pants. He regularly shines his shoes, and he keeps them in shoe trees. He always wears an undershirt and a belt. He wears a hat, like my grandpa did, to keep his bald head warm, and he genuinely had no clue that fedoras are even a thing until I pointed it out to him. When he is at work, he is a snappy dresser, almost anachronistically so.

So until we started dating, I really had no idea what his casual wardrobe was like. I eventually found out that it contained lots of souvenir T-shirts, an oversized UCLA sweatshirt, and some baggy jeans from the late 90s that really should have stayed in that decade. There were also some garments that I can only describe as your dad on vacation in Florida in 1989, but let's not speak of that. No, let's not speak of that.

And then there was the “blanket shirt,” as I called it with equal measures of revulsion and affection. To Jeff’s credit, he never wore it outside the house, but it was a button-down casual shirt that was at least three sizes too large for him, and made of some sort of unidentifiable fabric that managed to be both completely structured and yet totally floppy at the same time. Jeff claims (incorrectly) that I “made” him get rid of it, and every winter he laments its absence because it was just so warm.

For the record, I never once asked him to get rid of it. But I do remember making fun of it, and so when he said I made him get rid of it, I realized that I maybe shamed him into getting rid of it, without even meaning to. I SHIRT-SHAMED MY BOYFRIEND, YOU GUYS.

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Those who live in glass houses shouldn't like, throw stones, or whatever. Because I bought this hooded sweatshirt at a drugstore in Iowa for $10. And I wear it around the house all the time and also I dribbled toothpaste down the front. And yet my dude still finds me attractive.

So a couple of years ago for Christmas, I bought him some new jeans to replace his 90s jeans, a couple of non-souvenir T-shirts, a flannel that could replace his blanket shirt, and a nice cashmere sweater.

Purchasing these things for him was thrilling. It was fun to shop for him and then see him in these new, more modern clothes. And I was happy because he wore them and seemed to like them.

He isn't really the kind of guy who goes shopping often. Once a year he'll go to Ross and buy some new work shirts, but that's about it. At the time, I thought I was doing him a favor.

But I haven’t bought him anything since. The reason is because I’ve decided I truly do not care how he dresses, and also, maybe I made him feel like shit by implying that he somehow was not already good enough for me. Of course he is good enough, just the way he is, blanket shirt and all. And besides, if the tables were turned and he were to purchase clothes that he thought were more suitable for me than my current wardrobe, I might feel a little hurt.

I love Jeff for who he is as a person: kind, thoughtful, affectionate. Three years into our relationship, he still tells me he thinks I’m the most beautiful woman in the world. And I think he is terribly handsome, no matter what he’s wearing.

So. How important are the clothes that your S.O. wears? Would you ever date someone with terrible, horrible, no good fashion sense? And would you try to change them? And would you be upset if you found out your boyfriend or girlfriend hated the way you dress?

Somer is on Twitter, almost never, ever talking about fashion: @somersherwood.