The Best Socks to Wear with Winter Work Outfits

Let's discuss an important question today: which are the best socks to wear in winter with work looks? How can you keep your feet warm and still look stylish and polished?

I've always found it much easier to wear many shoes in the summer because bare legs are widely accepted. (Know your office, of course!) Once the weather gets colder, though, you suddenly feel like you're either risking freezing your ankles (at least), or getting ticketed by the fashion frump police.

We haven't talked about how to keep your feet warm with work outfits in ages, so let's discuss. What are your favorite socks, nylons, or more, readers? Which ones are the most durable and the most comfortable?

(The stock photo at top is the best I could find, but I think it illustrates the problem — does it look weird to you that she isn't wearing socks with a winter coat? If it does seem weird to you, then let's discuss what she should be wearing…)

The Best Socks to Wear with Boots and Work Outfits

Regardless of what height your boots are, I think if the entire top of your foot and ankle is covered you can wear whatever socks you want. You probably won't want to wear ankle or no-show socks just for comfort's sake, and for taller boots I've always preferred to have knee-high socks — but this is just personal preference.

Sock brands that readers have called out as being great include Bombas, Sockwell, Darn Tough, and Smart Wool.

What Socks Can You Wear to Work In Winter with Loafers, Mary Janes, Ballet Flats, and More?

There are a few different options here if you want to have some kind of sock for warmth but you're used to that “bare leg” look (like in the photo at top)…

The Best Socks to Wear in Winter with Loafers, Flats, and More

There are a few different options here if you want to have some kind of sock for warmth but you're used to the barefoot look (like in the photo at top). If the photo of a woman with a winter coat and bare feet looks ok to you, then skip this section… but if it doesn't, let's discuss what she should be wearing.

The main problem with shoes that you wear barefoot in summer (at least for me) is that if I wear them with regular socks, they are too tight. You can sometimes find very very thin socks, but for my money I think these are the main categories of sock options if one wanted to wear a more delicate shoe like a Mary Jane, ballet flat, or more.

Sheer Socks

This is a trendier look right now, but because they tend to be on the shorter side, it can be tricky to pull off unless your pants are full length — look for these at trendier workwear spots like Ann Taylor, J.Crew, and more. (Amazon also has a ton!) You will find a lot of crazy fun patterns, as well as a lot of sheer crew socks.

knee high socks, aka Trouser Socks

In my mind, these are a different category than knee-high pantyhose in a few important ways:

• they're a much thicker weave/denier (often thicker than tights!) and often opaque
• they snag a lot less and are a lot easier to care for
• they may come in a wide range of colors and prints (but are generally more sedate than the trendy sheer socks)

Look to hosiery brands like Hue, Falke, and more for these.

Knee-High Pantyhose, AKA Nylons

These are like sheer pantyhose or sheer tights… that only come up to your knees. They do make them with reinforced toes; you might also find them with fun details like patterns. A number of the previously mentioned brands make these, but you may also want to look to drugstore brands like Hanes, Silky Toes, and more. Nordstrom also has some!

Of all of the options, this one has been the furthest “out” in recent years because pantyhose have been out, and more and more offices are accepting of bare legs in general. But the sheer pantyhose look is coming back, though (often called “sheer tights” these days), so I wouldn't be surprised if knee-high pantyhose are on the upswing as well. (It's so trendy right now that you can even find fleece tights that look sheer.)

Tights or Pantyhose

Some women wear full-length tights or pantyhose, even beneath pants — some do this to be warmer, to make unlined pants more comfortable, or for some light shaping or compression. Here's our last roundup of the best tights, as well as our roundup of the best pantyhose.

How to Keep Your Feet Extra Warm in Winter

If your feet are always freezing, you may want to consider an option like fleece socks, either as knee highs or crew socks. Another option (harder to find right now): silk sock liners — check hiking stores or stores like Lands' End or L.L. Bean as we get closer to January. Both choices only add a tiny bit of thickness but a lot of warmth!

More Thoughts on Socks with Winter Work OUtfits

Should Your Socks Match Your Pants Or Your Shoes?

You can do either (or do a contrasting color also).

Can You Skip Socks in the Winter?

You do you, boo, but here are a few thoughts: at work your appearance should reflect important qualities about yourself, such as your judgment and general awareness of things around you. Skipping socks might make someone question those traits. Sure, it's always possible a coworker has decided to commute in warm, cozy boots and then switched to flats at the office — but do you really want your boss or colleagues to have to think of the exception?

The other problem here is that while nylons aren't hugely popular anymore, older generations are used to them — so even though they don't provide a ton of warmth, having the top of your foot or ankle be completely bare feels a bit… strange.

Ultimately I think it comes down to what we always say: know your office! If everyone midlevel or above at your office is wearing flats without socks, then go for it (if you would like to).

Readers, which are your favorite socks to wear with winter work outfits?

Stock photo via Pexels / Ono Kosuki.

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