Shorts and Socks Season

August, baby!

Here’s how I remember my life in shorts and socks.

1990: I showed up to school with a pair of basketball shorts and a pair of Jordan 4s. I thought I looked fly, but this kid I always hated whose name was Nathan, started making fun of my socks. I asked what was wrong with them, he told me they were too long, white, and had stripes. I had missed the memo that other 10-year-olds had made the rule that socks could only show up just above the ankle and could either be black or white, but couldn’t have stripes, it seemed.

1994: I showed up to skateboard with my friends wearing shorts, Airwalks, and no socks. My friends make fun of me. When I get home and smell my feet, I sort of understand why.

Sometime in the late-1990s: I get my first pair of no-show socks.

Flash-forward to the last few years and I find myself not caring what people think, but spending too much time thinking if I should or shouldn’t wear socks with a pair of shoes if I’m wearing shorts. Most of the time it’s a no when it comes to loafers, but I’ll make exceptions. A few weeks back, I wore an old pair of black Gucci horsebits, but decided to wear a pair of cream deck socks with them. The next day, feeling inspired by the classic old Polo ads, I wore another pair of deck socks with some canvas sneakers to hang out on the roof on a moderate summer day.

I’ve been slowly experimenting with socks and shorts over the last two summers. I really do find myself going back to that little jerk when i was 10 making fun of me when I’m deciding what to do, but then I’ll think about this little folder on my desktop I’ve got that I’ve been using to slowly collect pics of guys in socks and shorts. I’ve come around to thinking that it’s actually the perfect look for this time of the year, specifically as we go into September and the weather can play tricks on you, when the tempteture may say one thing but the real feel is another.

But I will say my mind started changing thanks to Armani in 1988. I was looking at this picture recently and couldn’t help but think this is really a strong, easy summer look that anybody can pull off even if you don’t have Giorgio cash. I do this a lot with a white T-shirt, a pair of khaki shorts, usually that I get from a place like Bronson, but Todd Snyder and Banana Republic are also dependable. I switch up the footwear and put on some desert boots. I think that’s the look. Chukkas and shorts? You look like you’re going to Jurassic Park or some shit. Love that.

But there’s also another thing I really like about shorts and socks that’s really the opposite of an Armani campaign. It’s hard to pull off, but I’ve seen a lot of older guys do it. It’s sort of this high art of schlub look that the gawd Samuel Fuller showed off in this beach shot from the 1980s. Everything here, the hat, the way the shirt is unbuttoned, the pen and paper in the shirt pocket, it’s all perfect. But dear lord, the socks and sandals is crucial here. The amount of chutzpah it takes to do this and pull it off is something you earn, and I hope to high heaven I get there someday.

I’ve been thinking about the shorts and socks thing as we roll through August because this is the time of the year that I really start trying to give up on summer. I feel like trash most days when I’m outside for more than a few hours. Hot and sticky, it’s not a good time to be a sweaty person. So I’m always looking for tricks to make myself more comfortable while also not totally giving into the instinct to dress like a slob because I can’t help but feeling like one. That’s sort of why I love socks and shorts. It’s not exactly a little pop for an outfit, but it adds something. Maybe it makes you look like you should be pushing a metal detector up and down the beach in Miami, but I don’t think there’s anything wrong with that.