No other item of menswear is more hotly contested than shorts. The debate as to whether it’s “appropriate” for men to wear them or not has circled back and forth over the internet for the last few years. In 2011, designer Tom Ford declared, “A man should never wear shorts in the city. Flip-flops and shorts in the city are never appropriate. Shorts should only be worn on the tennis court or on the beach.” This prompted strong reactions from defenders of shorts, including a, let’s call it, strongly worded takedown of Ford’s opinion on Deadspin.
In 2015, in an interview with Elle, social critic and author Fran Lebowitz added her own commentary on men’s leg wear: “It’s disgusting. To have to sit next to grown men on the subway in the summer, and they’re wearing shorts? It’s repulsive. They look ridiculous, like children, and I can’t take them seriously.”
Frankly, it’s Lebowitz’s opinion that is childish. Men can wear shorts if they want to (except for cargo shorts, which the world has apparently decided to shun entirely). And plenty of intelligent folks have advocated in favor of shorts, especially in recent years, and further, many have done the unthinkable, adopting the garment for non-casual situations as well. But even if Ford and Leibowitz’s ideas are out of touch with modern sensibilities, they do touch on a larger point that, even in an era where shorts have been widely accepted as a reasonable fashion staple, they can be difficult to pull off.
I’m a stereotypically neurotic millennial dude. I have my insecurities, and my legs have always been one of them.
But for as vapid and illogical as the anti-shorts argument is, I myself have rejected the “sky’s out, thighs out” mentality for years now.
And I’ll level with you why: I’m a stereotypically neurotic millennial dude. I have my insecurities, and my legs — pastier than the cast of a Tim Burton flick, visibly hairy but not hairy enough to be attractive in a Connery/Selleck/Reynolds fashion and, well, let’s call them thick — have always been one of them. I simply can’t bring myself to subject the world to my legs.
So shorts have been a difficult sell. Getting the length is tricky: too long and they look silly, too short and they show off too much of the aforementioned tragedy that is my lower half. The fit is tough, too, because most cuts are tight enough to be uncomfortable, and if they’re too loose they’ll make that damn “swooshing” noise and, again, are ridiculous-looking. Even if I find the right shape, it then opens up another can of worms — what shoes actually look good on me with shorts? No shoes actually look good on me with shorts — believe me, I’ve tried everything from slip-on sneakers to wingtips.
