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Style Thief: How To Dress Like League of Their Own’s Heartthrob Pitcher Max

Max Chapman and Carson Shaw have my favorite fashion arcs in A League Of Their Own‘s first season. We watch them go from wearing what they think they’re supposed to wear to wearing what they actually want to wear. There’s some experimentation and play, their confidence in their looks increasing alongside their confidence in their baseball skills. For Max, that means trying out more and more pants looks and playful pieces like vests. I also like that Max has very specific colors she knows she looks good in and largely sticks to them. Dark red and dark blue are her go-tos and they do indeed look great on her. Sometimes, she mixes in some olive. Basically, Max is an autumnal icon.

Previously in this series: a guide on how to harness the high femme floral looks of A League of Their Own’s Greta.

Casual Hot

Like!!!! This is the simplest outfit ever, and yet, she is making it seem like a work of art. It’s the perfect look to wear while leaning against something, as she’s demonstrating. Who can resist a casual-hot lean? I have not been able to pull off a newsboy cap like the one Max is sporting here — though I have attempted it at many junctures of my very gay life, especially when I was experimenting with a more tomboy femme/soft butch aesthetic several years ago. But a newsboy cap on other people? ABSOLUTELY YES. LOVE IT. The tank + high-waisted trouser + unbuttoned buttondown is a v versatile casual-hot look you can rock just about any season, any occasion. If you’re a Max in your heart, make this combo part of your capsule wardrobe.

Loose Buttondowns

Speaking of capsule wardrobe, Max’s closet had gotta be just brimming with red, blue, and olive buttondowns in long and short sleeves with loose/boxy fits. Tuck any of these shirt options into some high-waisted jeans or slacks, and you’re good to go. Don’t love any of the three shirt options I linked? Just Google “short sleeve resort shirt” and you’ll find plenty of other options. I recommend going with a linen or linen blend version. This is truly Max’s go-to look, and she wears the hell out of it. As for styling, you can do this outfit with a pair of sneakers or ankle boots. And of course, if you’re wearing a literal Max costume, you gotta get a red-brimmed blue ball cap.

Party Vest

Party! Vest! I found a slightly more modern take on the suiting vest here, but you can definitely find a more vintage look, like this version which is on sale for $50. While I’m a big fan of the buttercream blouse, the vest really is the star of this look, and once you have a vest, you can become the Vest Dyke of your dreams. This style of vest will instantly dress up any shirt. Or, go bold and go shirtless underneath (though that feels less Max, more Shane, of course). And have fun with lapel pins on your vest! It’s a great way to add a pop of personality.

Coverall Chic

Here are just three different versions of navy coveralls, because why not! For truly the best coveralls, I recommend actually thrifting Dickies or a similar work brand and then having them tailored. Also, Max + Clance would be a v good best friend x best friend costume idea this Halloween just saying.

Now go forth a build a capsule wardrobe full of dark solid buttondowns and high-waisted trousers and denim. You’re ready to live your best casual-hot life. Stay tuned for a guide on how to dress like Carson Shaw next week in an all-new Style Thief!

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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 847 articles for us.


  1. Thank you for this! After the first year of the pandemic I was pretty sure that I was never wearing a buttondown again – knit tops are so comfy! But that plum buttondown is calling my name.

  2. I may have paused mid workday to buy some of these things. Now I’ve got a few days to prepare myself for the disappointment when they don’t automatically transform me into someone who looks as good as Max does when I put them on.

  3. So many of the outfits on ALOTO (not just Max’s) include outstanding long-sleeves button down shirts which I must say is a perfect inspiration for autumn in the northeast.

    These style thiefs are so fun although I share another commenter’s suspicion that I need to prepare myself that will never pull off these looks in a way that is wholly satisfying after seeing them on Max (or Greta or Carson etc).

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