We’re willing to bet you’ve got most of the basics covered as far as putting together a stylish winter ensemble is concerned. There are elements like the all-important winter peacoat or topcoat, a thick-knit sweater, those cozy corduroy pants and ideally, a great pair of refined yet weather-ready leather boots. But before those elements can synchronize in perfect harmony, consider that critical final step: Sliding into a pair of warm dress socks.


Shop Wool Dress Socks


Retaining your edge in terms of refined style needn’t mean wearing a pair of socks destined to leave your digits out in the cold (figuratively, if not literally). Warm men’s dress socks are an essential not to be overlooked. It doesn’t quite matter how warm your winter sweater happens to be if your feet are uncomfortably cold during a holiday parade or a day at the tree farm. Let’s consider all the basics to keep in mind as you reinforce your sock drawer against old man Winter by finding a pair (or two, or three) of winter dress socks.


warm merino wool dress socks in rich olive green


What Should I Look for In Warm Dress Socks?

Dress socks for winter ultimately share a lot of the same DNA as the best socks to wear with boots. Fabrication, first and foremost, is key. While some dress shoes and wearing occasions call for socks with a more fine weave (like tuxedo socks in traditional black, for instance), winter is a time to embrace a touch more texture and a thicker weave. For us at Boardroom Socks, that means embracing the power of Merino Wool Socks, especially in the over the calf length for which we’ve become so famous (if we do say so ourselves). It should come as no surprise that the material makes for great winter dress socks.

striped wool over the calf dress socks worn by model

What exactly makes that fiber part of some of the best warm dress socks? Merino wool is a marvelous fabric occurring naturally in the wild (it’s harvested from Merino sheep), and it’s got a laundry list of famed properties. It’s a natural temperature regulator, so it helps to keep your feet warm, while also wicking away sweat so you don’t overheat. That’s part of the reason it works so well in items like crewneck T-shirts and henleys, but let’s focus on warm dress socks for winter.

Our over the calf length, or any sock that provides extra coverage, naturally delivers more warmth, since less skin is exposed to the elements. That coverage should prove handy for evening strolls as well as extended periods of time traversing the town under starry seasonal lights.

Warm Dress Socks Shouldn’t Skimp on Style

Part of the fun of dressing in the fall and winter, particularly when it dials down to winter dress socks, revolves around embracing color and pattern. While you’d opt for vivid colors and bright floral patterns in the spring and summer, from your shirting to your socks, rich, darker colors make for a stylish pair of winter dress socks.


charcoal grey dress socks with dark grey slacks and brown dress shoes


We prefer colors found in our Charcoal Over-the-Calf Dress Socks, as well as our Olive Merino Wool Dress Socks – both colors work with earth tones and with shades of tan or even burgundy and navy. Even Brown Merino Wool Socks can prove a nice change of pace aside from Heather Grey, Charcoal or dark blue socks.

And don’t discount the importance of a dash of personality and vibrant style as you step into a pair of dress socks for winter. That’s where our Fair Isle Socks hit the mark (again, in our humble opinion). These represent our thickest, heaviest socks, and they’re great for more casual wear on cold winter days, particularly with your favorite pair of handsome leather boots.

man wearing grey Fair Isle patterned wool socks sliding on leather dress boots

Take heed, though: They’re too casual for properly dressy situations (like a black tie holiday soiree or any occasion where a finely tailored winter suit is your style move of choice), and they’ll prove too thick to wear with dress shoes. That being said, they’re a toasty alternative for casually rugged style.

Socks Make… The Man

You could say many things “make” the man – the proper winter suit, a finely cut overcoat, a warm yet tasteful beanie or scarf. Like we said earlier, those are all for naught if your feet aren’t comfortable in the colder months. The best warm dress socks regulate your temperature (as with merino wool), and they come in rich seasonal colors like Olive or Charcoal.


Shop Wool Dress Socks


For more casual coziness and serious winter style points, wool Fair Isle socks are another Boardroom Socks-approved recommendation. And opting for extra coverage with Over-The-Calf Dress Socks – like the ones we sell! – is always a safe bet. Banish winter cold (temporarily) by building a look from the ground up with warm dress socks for winter.

Editorial Staff
Editorial Staff

Our editorial staff is comprised of menswear experts dedicated to providing you with helpful information. Sharing everything from style tips to sock care instructions, these gentlemen are a wealth of knowledge for both our customers and the Boardroom Socks team.



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