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Style Thief: How To Dress Like League of Their Own’s Butch Icons Lupe and Jess

A League of Their Own has gay looks for everyone — from the high femme stylings of Greta to the fly butch flair of Jo and in between with Carson and Max’s versatile presentations. Today, we’re going back into butch territory with beloved hermanos Jess and Lupe.

Jess and Lupe have distinct but complementary go-to butch styles. Jess has never met a sleeve she didn’t roll, preferring short-sleeved buttondowns that she leaves unbuttoned over white, undershirt-style tees. Lupe plays a little more with patterns and stripes, also enjoying a short-sleeved buttondown but usually wearing it buttoned. They both look very good in hats, which is a well known butch superpower. Below, find some slightly more modern takes on their looks so you can emulate their easy tomboyish swagger.

Always Be Rolling

Jess in A League of Their Own wears a blue short-sleeve buttondown with the sleeves rolled up over a white tee with trousers and a blue ball cap. Photos of: A denim short-sleeve shirt, a white t-shirt, blue trousers, and a blue ball cap.

1. Denim Shirt ($90)
2. White T-Shirt Multipack ($18)
3. Trousers ($90)
4. Ball Cap ($12)

Again, Jess has never met a sleeve she didn’t roll. The gal simply loves to roll her sleeves! Listen, if I had baseball arms, I too would never ever cover my arms. I do often attempt a rolled sleeve, but they can be finicky/not stay put. Jess has this figured out though, usually opting for short-sleeve buttondowns made of sturdier material like a denim or a chambray so the roll stays in place. As for a shirt to go underneath, this is where multipacks come in handy! Why buy just one comfy white tee when you can buy three? Like this look? Then you’ll probably want to revisit the Jo style guide, because it’s all about the art of butch layering.

A Look To Lean In

Ah, yes, the butch art of leaning casually against a wall. Of course Lupe is fucking good at it. By the looks of this photo, she invented it. Truth be told, you can lean in any outfit if you’re confident enough. But something about a slouchy/boxy tee really is the ideal leaning look.

Just a Really Good Shirt

As I said up top, Lupe gets a little more playful with patterned shirts than Jess does. This is a great chance to get into some butch florals! Here are four different styles of buttondowns in prints and patterns to choose from. Throw one over a pair of high-waisted jeans ($98) with or without a belt, and you’re good to go out for a night of dancing or just for an intimate dinner.

All Aboard

Okay, so it’s kind of giving train conductor, but I like it? I will absolutely board this train if you know what I mean. Obviously, I took some liberties with the hat here, but I tried to modern up the look. Jess wears pants so fine they’re worth being fined for, so invest in some sturdy high-waisted pants to rock with various rolled-sleeve buttondowns.

Butch Night Out

Let’s hear it for paisley! You simply cannot go wrong with paisley for a gay night out on the town. Pair it with an oversized blazer, and you’re unstoppable. Faux leather and silky, paisley tops are two things that have a sort of femme-ier reputation, but they can absolutely be butched up, especially with the right accessories and shoes. When in doubt, just wield a beer like an accessory the way Lupe is here.

That should just about wrap up the queer style guides for A League of Their Own. If you have any other queer fictional characters, celebrities, etc. who you want to learn to dress like via Style Thief, drop a comment below! I’m thinking of tackling some of Eleanor’s looks from Do Revenge next.

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 861 articles for us.


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