Gone are the days when men had to match their socks with their trousers. That means wearing black socks with black trousers, dark grey socks with charcoal trousers, blue socks with your blue jeans, and so on. Things are different now, for adventurous dressers especially and that’s with colored socks. With colored socks, your trouser doesn’t have to match the socks though it requires a little more care but it can definitely look great. You need to bear in mind that wearing bright colored socks doesn’t match every outfit hence you can only wear them when;
You want to liven up a simple outfit. Got something basic going on for the day? A pair of unique socks turns something like a jeans/T-shirt or khakis/collared shirt combination into something that seems a little more deliberate. It’s like a pocket square in a jacket — it tells people that you don’t look this way on accident. You put some thought into the outfit.
You want extra color-coordination. Been reading about your complexion and your best colors lately? Show them off with some subtle matching. A colored sock that complements something else in the outfit is a nice, detailed touch. Work your sock into the same color scheme as your pocket square, your shirt, or even your sports jacket or sweater to get a coordinated look.
You know you’ll be doing business in your stocking feet. Not every business culture keeps its shoes on all the time. When you have a reason to believe your socks will be on display, go ahead and make it fun — so long as you’re not planning on doing serious business with conservative people. Anything from a locker room to a corporate spa to a meditative retreat might end up with you shucking your shoes, better to be prepared.
Beyond those specific situations, there’s also the simplest and best time to wear colored socks: when you feel like it. You just have to do it right.