Dean writes: Okay, you’re the one men’s style blog that never seems to have an off day, and I have a question. In the summer – it gets hot here – I tend towards shorts, and realize it’s not a good style move. As the weather gets warmer, is there any stylish way to wear shorts? My problem here isn’t the shorts themselves, but the choice of shoe, and sock (if any.)
First of all: good work on that “never have an off day” intro. Flattery will get you everywhere. Leaving that aside… as the weather starts to warm up, I’ve been getting a lot of questions about summer, uhm, legwear. So here’s my spiel.
First of all, you’re right in thinking that shorts will always look less elegant than pants. The fact of the matter is that shins and knees are weird-looking, especially on guys. That’s just reality. When I lived in a climate that accommodated it, I didn’t own any shorts. It’s very easy to look lousy in shorts.
Then I moved from San Francisco to Los Angeles, and found that one of the many downsides of the move was a sudden pressing need for hot-weather legwear. I really fade fast in the heat, so I have to really be careful not to overdress when it’s hot outside. That meant I had to buy some shorts.
So here are some guidelines:
When you don’t need shorts, avoid them. If it’s in the 70s or 80s, you have lots of other options. Lightweight chinos, cotton trousers, linen pants, even tropical-weight wool. You can roll the hem up a bit if you’re not afraid of current trends and go without socks to enjoy the wind on your ankles. Unless you’re on a boat or at the beach, you can usually keep those legs covered.
If it’s just too hot, keep it simple. Clean lines are your friend when it comes to shorts. Length can vary somewhat according to preference, even among the style-obsessed. What’s important is that you avoid the baggy, cargoed look that shouts “I’m another schlubby American jackass." If you have trouble finding shorts you like, don’t be afraid to have a tailor hem a pair of pants for you – it’ll cost you ten bucks.
As far as footwear, save your sandals for the beach. Lots of shoes can work well with shorts, but the classics are simple canvas sneakers, worn sockless (or with no-show loafer socks). Loafers work fine, though they can look a bit Tommy Bahama / dad on his day off if the rest of your outfit doesn’t look sharp. Boat shoes are also classic, though at this point, at least here in LA, they have very nearly passed from hipster-ubiquitous to just generally ubiquitous, so I might hold off on those. Canvas boat shoes are a nice compromise there. Even bucks or saddle shoes can work.
The central challenge of wearing shorts is a bit like the challenge of getting dressed when you’re fat. You don’t get the benefit of the doubt. You have to prove that you’re not a sloppy mess. Your game has to be tight. But it can be. Have faith.