The basic rule of thumb for men’s socks is an easy one:
The color of your sock should match the color of your trousers.
That means wearing black socks with black trousers, dark gray socks with charcoal trousers, blue socks with your blue jeans, and so on.
But that’s boring
Yeah, it’s a good rule that keeps most men looking sharp and will always be appropriate for business settings — but for adventurous dressers, it gets dull after a while.
So what about mixing it up?
There’s absolutely a place in men’s style for colored socks that do not match the trousers.It requires a little more care, because it’s not a simple, neutral choice, but if you take that care it can look great.
“Bright” socks can mean a lot of things: bold solid colors, classic patterns like argyle and paisley, on up to things that are bordering on novelty items (cartoon characters and so forth).
In general, none of those are going to cut it as part of a serious business outfit or a somber occasion like a funeral. These situations are not about you expressing individuality – they are about you showing respect and fitting in.
Now, there are exceptions to the rule. There are some powerful men out there who’ve worn custom-tailored suits with handmade Italian shoes — and a pair of red or lavender socks.
Those guys know what they’re doing. They’re making a bold statement, almost a challenge. The business suit with colored socks is a look that says “Yes, I know the rules, and I’m confident enough and care enough about how I look to break it anyway, because it’s more fun for me. Deal with it”
All well and good if you own a Fortune 500 or are a former Army Ranger. The rest of us should think of our brightly colored socks as social wear, and leave them out of any full business dress.
Now that we’ve gotten that out of the way, here’s the good news: if you’re not in a suit-and-tie formality sort of situation, you generally have the option of wearing colored socks if you want to.
It has to be done right — you can’t just throw them on with anything — but there’s usually a way to make it work.
Why would you, though?
There are a couple of times when you might specifically want colored socks, beyond just enjoying them for your own sake:
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.
When you want extra color-coordination. Been reading about your complexion and your best colors lately? Show ’em 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.
When you know you’ll be doing business in your stocking feet. Not every business culture keeps its shoes on all the time. In places like Japan, shoes are often removed for meals, or sometimes even for drinks. 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. You don’t have to go to Asia for sockless situations, either; anything from a locker room to a corporate spa to a meditative retreat might end up with you shucking your shoes.
Beyond those specific situations, there’s also the simplest and best time to wear colored socks: when you feel like it.
So long as you’re putting some thought into how you’re strutting your gussied-up ankles, there’s no reason you can’t play around with your socks in your basic, day-to-day, “just going about life” sorts of outfits.