Dave asks: I just saw Derek’s post on plimsolls. I picked a pair up for the summer recently and coming from the high-top world primarily I’m not sure exactly what the recommended sock situation is for these. Navy/dark socks, or a white athletic sock (these are navy shoes, by the way)? A shorter sock, a no-show sock, no socks at all? Does it event really matter if I am wearing pants?
I’d say that this is one that depends on context.
There are plenty of situations where no socks (or no-show socks) are perfectly appropriate. Typically with shorts for example, socks will just look silly. Similarly, there are plenty of folks interested in a summertime breeze on their ankles who prefer a sockless look. This can be particularly appealing with a slim pant that’s rolled at the ankle (the “I subscribe to the Sartorialist” look). No socks has the convenience edge here, but no-show socks have the “less gross” edge, and will do less damage to your shoes.
When I’m not wearing shorts, I usually wear crew socks with sneakers. I’m not crazy about white tube or gym socks when I’m not exercising, but some cling to them. I certainly can’t recommend wearing black socks, which will make you look like a grandpa (in a bad way). I generally wear more brightly colored casual socks when I’m wearing plimsolls with casual pants like jeans or khakis. I love these ones, from Lands’ End, and if you’re lucky enough to live within access of a Uniqlo, you’ve got a near-bottomless supply of cheap ones. Of course, stores like H&M and Gap often have options as well. I find that a good pair of red socks are enough to punch a white-tee-jeans-and-white-sneaks outfit up a bit.