I remember the first time I wore a pair of truly ugly shorts out in public. It was junior year of college, the night of an '80s-themed dance. I had these oversized charcoal gray Levi's, high-waisted, that I'd hacked the legs off of and cinched at my waist with a belt. "Those are terrible," one of my male friends told me.
Damn straight. That's why they were so great. The Man Repeller approach to dressing is nothing new, so I shouldn't need to explain why the words "unflattering" and "cool" can be uttered in the same sentence.
In light of that, you can guess how delighted I was to happen upon these ugly-ass (baggy-assed) Rachel Comey shorts while trolling around online for summer clothing. They're fun and look great with a crop top and sneakers. Maybe toss on a baseball cap for good measure to round out the tomboy vibe.
Rachel Comey Rogue Shorts, $288, available at Shopbop.