For much of the year, I rely on navy wool over-the-calf socks. As many readers will know, I favor over-the-calfs because they stay up on your leg, thus ensuring your bare calves won’t be exposed when you sit down. I also find navy is a slightly more interesting color than black, and can be successfully paired with almost any kind of trouser.
In the summer months, however, long wool socks can wear a bit too warm, so I turn to other options. The first are still navy over-the-calfs, but instead of wool, I’ve come to really appreciate the highly breathable cotton ones sold by Dapper Classics. They sent me a few pairs for free last year and I’m really pleased with how well they’ve held up. Like with many high-end socks, however, I’ve found that solid colors hold up much better than patterns. For whatever reason, high end patterned socks seem to fuzz up and fall apart more easily in the wash. Still, their solid navy is made with a very durable, breathable weave, and you can feel the air whiff by when you put these on and wiggle your feet.
Another popular option is no-show socks, which Jesse has written about before. They’re essentially a short cotton sock that allows you get the look of being sockless without actually having to be so. In addition to the ones Jesse named, 2(x)ist also just released a collection of no-show socks. I have no experience with them, though I’m told they have a rubber grip at the heel that helps prevent slippage. Jesse also reviewed the Mocc Socks he named in his original article, and liked them.
I tried no-show socks a couple of years ago and sadly found they just didn’t work for me. Mine had rubber grips as well, but they still kept slipping off. So I’ve turned to terry cloth insoles from Aldos, which you can slip into your shoes whenever you want to go sockless. If your feet get sweaty easily, sprinkle in a little Gold Bond powder to keep them cool and dry.
Finally, summer being what it is, I like to wear sneakers a bit more often on the weekends. Dress socks are a bit weird with sneakers, so I pair mine with more casual cotton socks. Like Jesse, mine are from Lands’ End and Uniqlo. I’ve found the ones from Lands’ End hold up a bit better, though I like Uniqlo’s designs (mine are these in grey). Get whichever ones you like best, though I recommend staying away from the white ones. Those just look too much like athletic tube socks, which in my opinion, should be worn only when you’re exercising.