The Necessary Elan for Wearing Men’s Clothing

First of all, I am writing this post from the perspective of a cisgendered woman, so I am referring to wearing clothing that either does not belong to me, or was purchased contrary to the manufacturer’s instructions. Off-label usage, if it were. Ignoring the most very basic rules of traditional fashion with wild abandon.

Mostly, I am talking about stealing Boyfriend’s clothing. He doesn’t mind a pair of socks here and there, or the odd t-shirt for sleeping. But this is about the peculiar style that comes about from wearing his clothing out and about.

The other weekend, for our closing show, I had not had time to do laundry and all my warm clothing was dirty. I had a t-shirt, some jeans, my boots, but no sweater. So I grabbed a sweater from the pile of oversized sweaters that even Boyfriend finds a bit too “relaxed” a fit for him. Needless to say, I was comfortable and warm, which was the main point. I was going to be running around, inside and out, gathering props and costumes after the show. I threw it on with a pair of jeans tucked into my riding boots, and didn’t give it a second thought.

Then, after the show, a friend of mine commented how stylish I looked and how much she liked my outfit. “Oh, this old thing?” I got to ask, cooly, although I did not cop to wearing a stolen sweater. And it got me thinking.

I had just come off the final performance of a fantastic run, where I played the star, and generally got to have my way around the stage for two weekends. I was at the top of my game, and plump with confidence. I think that is what made my baggy sweater and jeans look like something worn with style and flair, rather than just another sad girl wearing an oversized sweater because she can’t be bothered to keep all her stylish clothes clean.

Perhaps that’s true of all clothing; that what is required to look stylish is to simply look like you belong in whatever clothing you happened to put on. But I think there may be something deeper. There’s something particularly stylish about a woman who can particularly choose something that may not have been designed to be flattering to her body, but she chooses to wear anyway for comfort, not as a statement. It’s almost the opposite of the “normcore” trend, where you try to look intentionally awkward. Instead, I wear clothing without consciousness, and that’s when I tend to look at my best.

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