The 19 Greatest Shorts-Wearers of All Time

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Welcome to SHORT WEEK SHORTS WEEK, GQ Recommends’ appropriately abridged ode to the summeriest and calf-baringest of bottoms. Whether you’re a big-and-baggy boy, an above-the-knee fella, or somewhere in between, we’ve got all the thoughts, takes, and, yes, recommendations to make this your greatest, leggiest, most stylish shorts season yet.


The last few years have blessed us with an abundance of legendary shorts outfits. But as dope as that one Donald Glover fit pic is, we can’t help but remember the famous shorts-wearers who paved the way before him. Maybe it’s the grainy quality of the pictures they’re captured in or just our misplaced sense of nostalgia kicking into overdrive. Or maybe the outfits really were better back then! It’s not generally advised to dwell on the past, but there’s nothing wrong with a little reminiscing, right? Especially when that trip down memory lane yields an abundance of shorts-related style inspiration, a crystal ball teeming with shortspo for all your future fits. Over the years, inseams have risen and fallen, and though the shorts du jour will likely change with the times, the truly legendary outfits of yore still hold up today. So GQ spelunked our way through the cavernous Getty archives in search of the greatest shorts-centric fits we could find. Scroll forth, take note, and then pin these famously-beshorted fellas to your summer moodboard, stat.

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The 19 Greatest Shorts-Wearers of All Time

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