How to Style Men’s Dress Socks 101

Have you ever noticed a really sharp-dressed man? When you think about it, they’re not doing much differently than anyone else. His clothes are probably not more expensive. Chances are, he’s wearing a coat, tie, and shoes. He pulls his trousers and socks on one leg at a time, just like everybody. But, he’s dressed with intention. He’s not wearing anything not meant to be there. That includes his socks. Below, we’ve got a crash-course in how to style dress socks.

Keep it Simple

One of the biggest sins in menswear is trying too hard. Guys want to show they’re “into style”, especially when starting out. So, they’ll roll up to a party in a waistcoat, jeans, and a fedora-with maybe a pocket watch on a chain. Or, they’ll throw on socks with flaming (caliente?) tacos on them for a date or (worse) business meeting. It’s too much.

Less is more in menswear. Classic and versatile styling means stripes, small patterns, and solids. Build a base of blue, brown, and grey. When in doubt, throw on a navy blazer, grey flannel slacks, and some polished penny loafers for a business meeting.

Is it the most exciting thing? Will it help with our next level? Absolutely.

Coordination Is Key

You can absolutely have fun with your socks. Here at Boardroom, we encourage it. But, your first goal should be coordinating.

When you’re wearing a suit in a conservative business environment, look first for a sock in the same color as the suit. Navy socks for navy suits; grey socks for grey suits; khaki socks for khaki suits, etc.

If you’d like to be a little more playful, look for socks in complementary colors. Burgundy dress socks with a navy or grey suit are nice indeed. Purple socks with olive or khaki chinos are unexpected, but work quite well, too.

You can bring in some pattern as well. If you’ve got a charcoal suit, try socks with pale pink dots or deep purple stripes. Navy suit? Go for orange dots, or even tri-colored dots to spice up an otherwise conservative suit.

We’ve also written extensively about how to pair socks with patterned suits, as this is where the game gets far more interesting. In general, socks with stripes tend to look best with solid suits or those with small patterns- think sharkskin and birdeseye/nailhead. Socks with smaller patterns like dots or squares work well with solids, of course, as well as as a sharkskin. Checks, plaids, and Prince of Wales style suiting also works well here, too. If bolder style is your thing, feel free to go for it!

The Right Shoes

The world’s best hosiery doesn’t matter much if you don’t have the right shoes to go with it.

Should dress socks be worn with dress shoes? Yes, obviously-despite how many men I see wearing athletic socks with their dress shoes. I think men may do it for a few reasons.

First, either through vanity or lack of knowledge, many men wear shoes at least a half-size too big. So, they’ll use thicker socks to compensate. Or, they find dress shoes uncomfortable (which, of course, could stem from the first problem), so resort to thicker socks for cushioning. Or perhaps, in this more casual age of dressing, they don’t wear many jackets or dress trousers. So, they’ll skip dress socks entirely-meaning that, on the occasion they need to be in coat and tie, they’re ill-prepared for it.

This brings us to an interesting consideration: can you wear dress socks with non dress shoes? Yes and no. Wearing silk dress socks or ultra-thin, 240+needle construction socks with your trainers is probably a no-go. Aside from the clash in formalities, even the sleekest sneakers have too much space for a superthin sock. Your feet will slop and slide around. That gets uncomfortable quickly.

However, here at Boardroom, we’ve developed a middle ground (168 needles, to be exact) for socks thin enough to be sleek for dress shoes, but still thick enough to wear for casual as well. I’ve worn my Boardroom Socks with suiting, as well as with both my minimal white sneakers and the ultra-cushioned New Balance 420s I use to take my daughter to the playground.

Style is Fun. Do it for You.

If you’d like a red sock and navy suit combination, go for it. Or, pale pink and grey? You bet. In what I hope has become a recurring theme for regular readers of the Memo, style should be fun. Express yourself. Enjoy the journey. Explore different combinations. Some might work. Others won’t.

Sure, you’ll get compliments on your style. And that feels fantastic. You stand a little taller, give a two-finger ‘thank you’ salute to the passerby as you go on your way. You might stand a little taller. Or, smile a little to yourself because you know you nailed that day’s look.

But, don't do it for random compliments. Or likes and comments on something as vapid and ephemeral as a social media post. Do it for you.

And that’s the Memo.

Yours in Style,

Tony Gorga
Boardroom Socks

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