Matching Your Dress Socks Is Easier Than You Think The Dress Sock Game

Let’s get something straight right off the bat: it’s sock season. In the summertime we show more ankle than an Amish stripper (without stinking up our shoes, we might add) but when the leaves start to fall and the temperatures do too, we open up the sock drawer and so should you.

You’ve probably got more socks than any other item in your wardrobe. Every guy should have at least 10 pairs of dress socks that he can count on to get him through a couple of weeks at work without doing laundry. But they don’t have to be a bunch of tired black, blue and gray socks that draw nothing but yawns from just about everyone who’s ever laid eyes on them (including you). So how do you step up your sock game? Scroll down.

In search of the perfect pair of socks we turned to sock guru Vincent Nasserbakht who manages his family’s sock emporium, The Sock Hop, in New York’s Nolita neighborhood. Nasserbakht gave us the rundown on all the things you need to know and questions you should ask yourself as you build the ultimate sock wardrobe. First, we’ll break down the key signs of quality you should look for:


Now that you know what goes into a quality pair of socks, it’s time to start making style choices. First off, how high should your socks go?

Once you’ve determined which length of socks work for you, it’s time to consider colors. Some men shun strong colors while others seek them out. As we’ve noted on The Compass in the past, we like to mix things up a little at the ankle. A pop of strong color in the socks is one of the few ways to be bold and stand out a little without overpowering your whole outfit. “It’s like a release valve for guys who are really boxed up all day,” says Nasserbakht, adding “you can get away with orange socks in more places than you can get away with an orange shirt.” Still, the choice is yours. 

If you’re really looking to mix things up downstairs, there is one way to wear multiple colors. Bring a pattern into play. Patterns can be tricky to pull off, but when done well – the payoff can be huge.


Now that you know what to look for in a well-made pair of socks, you’ve considered the different style options and you’re ready to fill your sock drawer with a killer collection, you may be tempted to order up 15 brand new pairs at once. Not so fast. Before you’re ready to fill your sock drawer with a killer collection, get to know what’s most comfortable for you first. Experiment with a few different brands and options (we like Bresciani, Falke and Mack Weldon for a good combination of construction and style) and figure out what works for you. Once you find the type of socks that feel best on you, the sky (well, technically somewhere around the top of your calf) is the limit.

How are you adding to your sock wardrobe this fall? Leave a comment below.

Special thanks to: Vincent Nasserbakht and the team at The Sock Hop for their assistance in putting together this guide.