The Best Men’s Dress Socks from Classic to Stylish

By Beau Hayhoe  |  August 3, 2022

The Best Men’s Dress Socks from Classic to Stylish
Courtesy of Boardroom Socks
 

Great style is all in the details, or at least, that’s what we believe at WERD. And those details can shine through both subtly and stylishly, whether it’s the watch on your wrist or a pair of the best dress socks on your feet. Yes, great style often starts from the ground up, and if you’ve put a lot of thought and research into the dress boots or shoes on your feet, you’d do well to take that same approach to shopping for a pair of dress socks. 

Above or below the calf?

Dress socks come in all manner of colors, textures and styles–true dress socks, though, should hit at your calf, if not above your calf (look for styles that note this with the terms “crew” or “calf” socks, or “over-the-calf” or “above-calf” socks). That way, your ankles aren’t exposed as your pants move while you sit down. Sure, wearing no-show socks with dress shoes is a trend these days–and it’s perhaps advisable to wear no-show socks with dress loafers in the summer heat–but when in doubt, go for maximum coverage. 

Should the sock color match the pants?

Another rule of thumb: Look to match your stylish dress socks to the color of your pants, or at least, in the same wheelhouse (shades of grey or black work with dark-colored dress trousers, for example). In some situations, you can opt for a darker shade of sock with a lighter pair of dress pants (for instance, navy socks with tan chinos), but (in our opinion!), you should swear off wearing ultra-light or white socks with dark pants. 

What dress sock material should I choose?

Fabric is crucial to keep in mind. You’ll find most dress socks are made from cotton or cotton blends with added stretch via nylon or polyester, the better to make them lighter and more breathable. Merino can also be incorporated in socks thanks to its anti-microbial, moisture-wicking properties

Do bold patterns work with dress socks?

One more note before we cover off on the best dress socks. It’s perfectly fine to throw in a bit of bold color or pattern with your dress socks selection, but again, when in doubt, subtle is best. If dressed ultra-formally for a boardroom meeting wearing, say, a classic charcoal or dark suit, keep your socks in the same color family as your pants and forgo a wild pattern. If, on the other hand, you’re in a more casual situation–perhaps one where you’ve paired up a blazer with an Oxford shirt and contrasting chinos–a touch of pattern works just fine. 

Now, if that seems like a lot of rules, bear with us: It’s not as complicated as it might seem. If ever you hit a fork in the road, go for subtle, stylish, classic dress socks. We think these WERDapproved picks are your best bet.



Best Everyday Dress Sock


Gold Toe Canterbury Cotton Crew Socks


 

There are times when it’s best to buy for quality rather than quantity (like when shopping for one of the best polo shirts, for instance), and there are times when you can get the best of both worlds, with a bit of added value thrown in the mix for good measure. Gold Toe makes it easy to hit all the right marks, using comfortable, soft mercerized cotton and nylon for both durability and a smooth feel on your foot, and the brand’s signature reinforced heel and toe are also markers of top-notch design.



Best Over-the-Calf Dress Socks


Boardroom Socks Over-the-Calf Merino Wool Dress Socks


 
$16.95

For the guy that wants maximum coverage, over-the-calf dress socks are the way to go, and you might say that nobody does it better than the aptly named sock purveyors at Boardroom Socks. The USA-made construction is a mark of premium quality, while plentiful color options should suit every palette and style. Bonus points for the fact that they’re made from soft, durable, highly useful merino wool for all-day comfort, day after day… after day.



Most Classic Dress Socks


Brooks Brothers Egyptian Cotton Ribbed Crew Socks


 
$19.50

It doesn’t get much more classic or timeless than Brooks Brothers in all manner of menswear essentials, from the company’s Oxford shirts to its crisp navy blue blazers. Round out any tailored look you can dream up with a set of finely crafted Egyptian cotton socks in a design that goes with just about anything in your dress wardrobe. The color is classic and versatile, the quality is second-to-none, and Brooks Brothers is certainly a name you can trust consistently when it comes to your basics drawer.



Most Versatile Dress Socks


J.Crew Ribbed Dress Socks


 
$19.50

If you find yourself needing to dress up often, you’re going to want plenty of pairs of dress socks. Enter J.Crew, designers of some of the most accessible, versatile menswear in America. Its ribbed socks are a classic dress sock style made modern, and done up in timeless colors to match plentiful dress trousers and suit pants. The cotton-nylon blend should prove durable yet soft, so we’d consider adding a pair in each color to your basics drawer.



Best Luxury Dress Socks


MR. P Gray Two-Pack Knitted Socks


 

The menswear giant that is MR. PORTER never skimps on the details, and that’s particularly true with the brand’s in-house, namesake line. You’re spending a bit more here to get a set of two finely crafted pairs of textured dress socks, made from a stretch cotton-blend for maximum comfort. Consider these a more “casual” dress sock to style with business casual looks, or wear them with dress boots and a more laidback, ever-so-slightly rugged fall or winter herringbone suit.



Best Splurge Dress Socks


Alanui Bandana Jacquard Cotton-Blend Socks


 

Are these pricey dress socks the most economical pick? Not exactly, but that doesn’t mean they’re not a heck of a lot of fun–and made with premium quality in mind, to boot. The eye-catching bandana pattern is a whimsical choice that’ll add some flash (in the right situation) to solid-colored dress trousers, but be sure the timing is right to rock some visually appealing pattern.



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