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I Want To Dress Like Lesbian Jimmy Buffett


As I continue down the road of my thirties, I’m feeling my style shift. I’m no longer shy about where I come from (Gulf Coast) and kind of want to own it? As a result, I find myself gravitating towards young Jimmy Buffett (RIP). The problem is I’m having a hard time adapting his boat lovin’, chill dude style to my tits and ass. Help me become Lesbian Jimmy Buffett?


The way I love this question!!!!!! As an Ohioan who grew up listening to Jimmy Buffett and eventually moved to Florida, I am so thrilled another queer is out here trying to emulate such an icon of queer Florida fashion. I, too, have some tits and ass myself, and I struggle to feel good in masc-of-center stuff just because…it wasn’t built for curvy people? I don’t have a solution that will fix all these problems immediately, but I have some suggestions (for you and me both!).

This might be a given, but my go-to is the Hawaiian shirt. It’s versatile and inexpensive; you can usually find them in various sizes. Since the general market for patterned shirts is older dads, a lot of them feature the most gloriously atrocious prints that could distract from and cover the chest area. I usually try to size up one or two sizes to achieve that go-with-the-flow, boat-life look. Even with a large chest like mine, wearing it unbuttoned with a sports bra or binder underneath still looks breezy, carefree, and 70s-style masc. If you don’t like the flowery prints, try getting inspiration from the Mamma Mia movies. I’m thinking specifically of that scene where Sophie and her dads are drawing on the boat.

Mama Mia still

As I’m googling “young Jimmy Buffett” to gather more inspiration, I’m noticing a few things (including the way he does the queer leg up/cross-legged/anything-but-regular-sitting posture in every photo). Cut-off jean shorts are a staple. This can be tricky with thighs and ass. When I try to go into the men’s section to find denim, nothing ever fits right. I’ve had some success looking for “boyfriend” style jeans in women’s sections. The lay of the fabric is supposed to be slightly oversized. Instead of searching for shorts in this section, what about getting jeans and cutting them yourself? You might want to watch a tutorial or two, but DIY baggy jean shorts scream Gulf Coast to me. If you don’t want to go the DIY route, you can always default to cargo shorts.

Then, there’s the matter of shoes. Obviously, barefoot is supreme beach vibes, but for when you actually need to wear shoes, you can go with boat shoes (if you want to lean more preppy) or “men’s” flip-flop sandals. You live in the South and have seen what white dads wear on their feet — it’s that. The more toned-down version of this could be sporting some Birks or a Chaco-type sandal.

Finally, there’s the grooming aspect. Jimmy’s look was always shaggy and slightly ungroomed, so I would encourage you to experiment with what that looks like on you. It could be growing out your hair and not shaving. It could also look like chopping and styling your hair to achieve a wavy, shaggy texture. Regardless of hair, if you add a gold chain or some nautical accouterments like a neckerchief with some aviators, you’ll rock it.

I hope these suggestions inspire you. I’m very excited about this lesbian Jimmy Buffett summer we’re having, and I’m thinking maybe we should reconvene in the comments in July to see what looks we’ve tried out?!

You can chime in with your advice in the comments and submit your own questions any time.

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Em Win

Originally from Toledo, Ohio, Em now lives in Los Angeles where she does many odd jobs in addition to writing. When she's not sending 7-minute voice messages to friends and family, she enjoys swimming, yoga, candle-making, tarot, drag, and talking about the Enneagram.

Em has written 73 articles for us.


  1. Men’s pants in “athletic” cuts (ie, more room through the hip and thigh)!!! Also, menswear with some stretch (these styles are often labeled something like “flex” or “comfort fit” or, confusingly, also “athletic”). The Gap men’s section has some great basics (bonus – most styles come in a 30″ inseam option).

    Also, I second the open shirt over a sports bra vibe. A white ribbed tank works great too.

  2. Maybe if you just want inspiration – or if you can swing the customs fees – check out Seasalt Cornwall. They do a mix of femme apparel and nautical inspired butchwear. I’ve bought multiple items from them, including a hyper femme floral dress, an amazing butch vest, a pair of twill trousers, a blouse, a cropped tweed jacket, and a shirt that I pictured as hyper femme that was a muddy blue that screamed “butch wedding attire” or as my partner said, “hawaiian shirt for women.”

  3. Hell yeah! Thanks so much for answering my question. I’ve already got a few of these pieces (so validating), but I’m feeling way more inspired on my quest to become Lesbian Jimmy Buffet.

    • It’s so cool to hear from LWs, Mads. Do you have any favourite brands? The other two I wanted to recommend to you was Wildfang and Sugarhill Brighton. I got an absolutely amazing cropped shirt from the latter which was turquoise and had various bright pink crustaceans printed on it. I think they’d be up your alley.

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