Q While they don't show much, I always wonder what color socks I should wear with black sneakers or other dark athletic shoes? Particularly when combined with casual work wear. I think of sneakers with white socks and I think of dark footwear with dark socks.
A Your instincts are right. I agree that in the past, to play it safe, it usually made sense to pair white sneakers with white socks and to match dark socks with dressier, dark footwear. But these days, it is not quite such a cut-and-dried single answer.
There was a time when wearing sneakers automatically meant white socks. This, too, is no longer the case. Dark sneakers, and even dark leather sneakers with white soles move the sneaker category into a somewhat dressier look. These should not be paired with white socks, but rather dark socks, and can even be paired with dressier dark socks or whimsical patterns that are on the market now. So, unless your office or social environment is strictly traditional and conservative, you can allow yourself more leeway.
All in all socks are a great way to add individuality and personality to the clothes you are wearing. When you are dressing for actual sports or athletics, and wearing white sneakers, then white, crew-length (above-the-ankle) socks still are recommended. If there's one type of sock to have in your drawer, it's crew-length socks. These classic socks hit just below the middle of the calf, making them a comfortable option.
As for dark, dressier shoes, "Your socks should match your trousers" is an old rule. Most men like it because it leaves no room for confusion and you cannot go wrong following it. On the other hand, many fashion-aware men with a sense of their own personal style prefer to coordinate their socks with their neckwear and shoes. Doing so enables them to introduce the newer wide range of patterned and perhaps lively-colored socks that conservative dressers would avoid. Though more difficult than the rule of matching your socks to your trousers, the tradition of coordinating your shoes, socks and neckwear also has a long history that can help liven up an otherwise dull outfit.
A few notes of caution: 1. When choosing multicolored socks to wear to the office, don't go overboard. If your tie is a vivid color, then repeating that color in the socks might be too much. 2. The sockless look is not appropriate for office/business wear. And even when it is appropriate, never actually go sockless: socks help your feet by keeping them dry, avoiding odor, giving your feet extra cushioning, and protecting you from blisters. If you like the look of no socks, wear no-show socks with your favorite sneakers or leather loafers. (I specifically mention loafers because it is my strong opinion that the no-socks look never goes with dressy, leather tie shoes.) Obviously, when wearing no-show socks, the color of the socks does not affect your outfit at all.
A last note, not all sneakers pair well with blazers and sport jackets and certainly not with suits (unless you are some start-up CEO trying to show off in GQ). Although many sneakers are extremely versatile, they are no substitute for dress shoes for serious business or formal events. You can get away with sneakers at many casual gatherings, but they are not meant for every occasion. The established rule is: when it comes to any special dress-up occasion, it is better to be overdressed than under-dressed.
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