The Cutest Shorts for Every Occasion

Many would argue that finding a great-fitting pair of jeans is the ultimate sartorial challenge. But I say flattering shorts are more difficult to p
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Many would argue that finding a great-fitting pair of jeans is the ultimate sartorial challenge. But I say flattering shorts are more difficult to p
Photo: American Apparel

Photo: American Apparel

Many would argue that finding a great-fitting pair of jeans is the ultimate sartorial challenge. But I say flattering shorts are more difficult to procure.

Shorts are something that, for most of my adult life, I've managed to avoid. Other than some old cut-off jeans, I've never kept a pair for more than one summer; after a few months of minimal wear, they always seem better suited to Beacon's Closet than my own. Because, really, what's to like? Shorts are more constricting than skirts, and unlike pants, they can ride up in a way that's neither attractive nor comfortable. Even as someone who does not have "issues" with the look of her legs, I never seem to find a pair that feels good enough.

But as this is the summer of Citi Bike, and I'm traveling via two wheels at least once a day, shorts are becoming more and more of a necessity. Dresses fly up, and pants—minus leggings or jeggings—are restrictive. So I've been hunting for all different kinds of shorts: dressy shorts, booty shorts, boy shorts, and more. Click through to see what I've found for all different occasions, body types and tastes.