Why One of Your Most Embarrassing Middle-School Fashion Choices Is the Cool Thing to Wear Now

Repeating pattern made up of polo shirt outlines and question marks.

(Image credit: Design by Katja Cho)

published 21 June 2016

Nobody should dwell on anything—much less middle school—too much, but hello? It's me? Wondering if after all these years fashion's current preoccupation with the official uniform of teenage lax bros across America is subconsciously a do-over in which the nerds and dreamers win? (Not a cry for help. I'm okay.)

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Thanks to physician-patient confidentiality, we'll never know whether it was an Italian Chad or Brody who motivated Miuccia Prada and Consuelo Castiglioni to resurrect the polo, but even without the complete backstory, we can determine that their appropriation is what gives it cachet. Make no mistake, however—this is not the Aéropostale/American Eagle/Abercrombie & Fitch logo-embossed model of your misspent youth (because, yeah, most of us were sheep at 14). This is Kip Dynamite. It's carousing on Lake Como with George Clooney. It's the outcast who found acceptance and success post-college and is now exacting revenge on his former tormentors by charging them $$$ for an elevated golf/tennis shirt, even though they're probably still too cotton-headed to understand the irony. (I swear I'm fine.)

A model walks down the runway at a fashion show. — Look at me now, Brent.

A model walking down the runway at a fashion show. — Take that, Spencer.

Now for the most important bit: how to wear one without dredging up long-repressed memories. Oh, and looking both chic and dorky, which, for mature adults, is considered desirable. 1) Seeing as how it's summer, go for a cotton-piqué or, even better, a loose knit. 2) On second thought, don't be afraid to embrace the #dadvibes, and go all in with longish shorts and slides à la Fendi's latest men's collection. On real dads, this is funny. On a girl, this is cool. 3) Tucked-in over untucked, usually. 4) Whatever you do, keep that collar un-popped, for the love of poetic justice and playing the long, vengeful game.

1. Carven, $170, net-a-porter.com; 2. Nikki Chasin, $150; nikkichasin.com; 3. Uniqlo, $15, uniqlo.com; 4. J.Crew Collection, $400, jcrew.com; 5. Zara, $36, zara.com.

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Chelsea Peng is a writer and editor who was formerly the assistant editor at Marie Claire. She's also worked for The Strategist and Refinery29, and is a graduate of Northwestern University. On her tombstone, she would like a GIF of herself that's better than the one that already exists on the Internet and a free fro-yo machine. Besides frozen dairy products, she's into pirates, carbs, Balzac, and snacking so hard she has to go lie down.