Got style? Got cold feet? I hear you! It’s a conundrum I didn’t take seriously until I moved to Ohio almost four years ago. But stylish women with cold ankles and feet want to know how to wear socks without “lowering the score” of their outfit. Me included! So I’ve done a lot research, a little thinking it through and a bit of experimentation, and I’ve come up with some tips to help us kick the socks-in-winter issue to the curb. Let’s learn how to wear socks with pants stylishly this winter.
Before we start the style tips, let’s just clear the air on a couple of things.
First of all, at our ages we’ve been around the city block enough times to be able to put our feet down on a few things. I don’t eat sushi, thank you very much. I’m 58 years old, and I’ve decided that’s not going to happen. I’m not going to jump out of a plane, ride a motorcycle or wear anything that exposes my midriff either. So as we broach the subject of wearing socks fashionably, let’s understand that you absolutely can wear your socks differently if you so choose. You do you. Own it and feel comfortable with your choices.
Second, let’s remember that this is a style blog. So we’re talking style here. If you want to wear your socks otherwise purely for warmth, that’s fine. Pull on the thickest, warmest socks you can find and call it a day! But it’s not necessarily stylish. And we’re talking style here today.
Choose the Right Shoes
The first fashion cue we need to take if we want to wear socks stylishly in the winter is that we must choose the right shoes. No, not all shoes look fashionable with socks. A stylish woman has to come to terms with that.
In my research I noticed that I never once saw someone wearing socks with ballet flats and calling it stylish. Nor did I see stylish women wearing socks with flats such as the ones shown above. I would opt not to wear the “flats” above if I needed to wear socks on my feet.
On the other hand, I frequently saw fashion photos of women wearing more menswear inspired footwear with socks. So shoes such as loafers, brogues and Derbies and Oxfords are great choices if you want to wear socks.
(Obviously you can wear socks with boots. But in this post we’re talking about socks with shoes and socks that show. And generally your socks don’t show if you have on boots.)
Brogues are shoes and boots defined by a low heel and multiple leather piece uppers which feature perforations called “broguing” and serrations. Oxfords are lace-up shoes with closed lacing, while Derbies, their more casual cousin, feature open lacing. Your husband, like mine, probably has at least one of these in his closet. And of course, most of us are familiar with loafers, which I’m showing in this post…because I don’t have the others. But obviously I’m not encouraging you to wear men’s shoes, just menswear inspired shoes. There’s a big difference.
Other than boots that have a shaft that fits under my pants, I only wear socks with my penny loafers in the winter. So that’s what you’ll see here. But I think any of the looks I’m sharing today would also work with other menswear inspired shoes.
Again, if your goal is style, I wouldn’t wear socks with ballet slippers, feminine flats or any open toe shoe. Yes, you may see some model-types doing this or you may see younger women pull it off. But I think that “throw caution to the wind” kind of style leap requires a “cool factor” that at least I do not have.
Consider your Pants Options
I found that exposed socks look great with pants that are cropped, ankle length or cuffed or rolled up a bit. I’ve also discovered that exposed socks look more on trend with looser fitting leg openings as opposed to skinny jeans.
I think this silhouette works best because it keeps the ankle looking thinner. Socks can add bulk. So by wearing a looser fitting pants leg, you create some contrast and space, and your ankles look leaner. As we age our ankles sometimes get a little thicker, so this seemingly small style choice can make a significant difference in appearance.
Wear Your Socks Like Undergarments or Accessories
You might assume that you should wear socks that match your pants…always. I used to think that. But as I scoured the Internet for fashionable images of women wearing socks, I discovered that nothing could be further from the truth.
So how’s a gal to know when she should wear socks that match her pants? This is perhaps the biggest fashion cue I’m offering in this post, and I think it’s the most profound tip that will help you bridge comfort and warmth with style.
Makes sense? I know this is a big leap for a lot of us. And it may feel risky at first. But I am thoroughly enjoying putting together outfits with socks now that I’ve been freed up to add a splash of color…or white!
I think a little of the pure white in my socks got lost in the processing of this photo. Trust me, these are dazzling white socks, chosen intentionally to contrast starkly with my black trousers and black patent loafers (similar loafers – more economical).
Check it Out! I’ve created a Pinterest Board with many of the images I found when researching for this post. Check it out. You’ll see that the vast majority are outfits in which the socks are treated like accessories instead of undergarments. In most every case they’re wearing contrasting socks to add color or interest.
3 Ways to Accessorize with Socks
Here are three fun and stylish ways to accessorize with your visible socks. Before I give you the style formulas however, I do have one more tip. In order not to add bulk (especially important for those of us with thicker ankles), consider wearing thinner trouser or crew socks that cling nicely to the ankle and foot. These may not add as much warmth as thicker socks, but that’s probably when you should opt for boots or pants that will keep your ankles unexposed anyhow. And if you choose cashmere blend or wool blend socks they should indeed provide plenty of warmth even if they are not especially thick.
#1 – Wear White Socks!
Have a little fun with your socks and go white. This is a stark contrast to an otherwise all black outfit of course. But you could do the same with jeans and a solid sweater or sweatshirt.
Here’s another similar look in a mirror selfie. I apologize for the poor quality, but it illustrates the concept well enough. Here I did choose off white socks to coordinate with the off white sweater I’m wearing, but the contrast is the same.
And that leads to my second style formula for accessorizing your outfit with socks.
#2 – Bookend Your Look by Repeating the Color at the Top
Recently I restyled this camel and red outfit that I showed earlier sockless and with pumps HERE. In fact, on the day we took these photos I wore this complete outfit to church. The temperatures were in the 20s and 30s all day, but my feet and ankles were perfectly warm as I went from point A to point B and as we snapped these photos.
Really this little trick makes it possible for me to wear my red pants on cold days. Otherwise I’d only wear them with heels or flats when it’s warmer. When your socks are not going to show except for when you sit down, you could wear them as undergarments and match them to your trousers, like I’ve done below. But I don’t think this looks nearly as smart as bookending with the color at the top of your outfit.
If you prefer to play down your socks, the above pairing is a safe option. But the problem then is finding socks that exactly match your pants. Easy enough when you’re wearing navy, black or maybe camel pants, but not so easy with, say, red or pink or peacock blue. But when you wear socks that mimic a color at the top of your outfit they don’t have to exactly match. There’s enough distance between the two to buy a little grace visually.
And you absolutely can bookend a look with coordinating socks when you wear jeans, too. But again, I’d choose to wear straight leg or even wide leg jeans, not skinnies. That space around your ankle is key.
#3 – Add a Surprising Splash of Color
I see now I need to take some new photos to illustrate this next style hack, but for today we’ll let these horrible mirror selfies suffice. I’ll try to slip some new ones in soon.
The next way to accessorize with your socks is to add a contrasting splash of color to your outfit.
Above I wore a monochromatic jeans outfit but then added a splash of red with my socks. This outfit still looks pretty conservative and smart, but that little bit of red adds some whimsy and joy. Some will argue that wearing red socks breaks the leg line visually and throws off the proportions. But actually if you’ll tuck your top and belt like I did, then you maintain those 1/3 to 2/3 proportions very nicely.
Here’s a similar look with black jeans, a black sweater, black loafers and gold socks. Because it’s a tonal outfit you really don’t have to worry about proportions at all. And that little touch of color really adds some life to this look.
And honestly, without the contrasting socks, these tonal outfits look quite boring and even a little strange. Everything just all blends together and you look a little “blobbular.” Yeah, I made that word up. But it fits, trust me.
What about print socks? Honestly, I didn’t see many print socks at all when scouring the Internet for inspiration. I suggest keeping all the flowers and puppy dogs and rainbows out of view, say under your boots. But if you want to wear something besides a solid, I think it’s smart to choose something subtle and a little sophisticated like stripes or argyle. Maybe something like these Bombas trouser socks or these Ralph Lauren prints.
How NOT to Wear Socks with Pants in Winter
I think it’s important to clear up a common misconception. You might have assumed that it would be smart to match your socks to your shoes. But this is actually a no-no that I saw mentioned throughout my research.
The reason you should not match your socks to your shoes is that you actually want a clear delineation between your leg or ankle and your shoe. The outline of the shoe should clearly be seen.
See the difference? Matching your socks to your shoes muddies the water, so to speak. You’ll look smarter and more stylish if your loafers are shown off with contrasting socks.
One Final Option
If you prefer not to have socks showing at all, but would like at least a little of the warmth and comfort socks can provide, I suggest you check out this sock brand. I love their no-show socks. And they’re not just for sneakers. They have no-show socks specifically designed to be worn with:
And yes, these socks really do stay in place with wear, at least on my feet.
Remember bottom line, you do you. But if you really want to look stylish wearing socks this winter, I encourage you to keep the tips I’ve shared in mind and to try one of the three style formulas I outlined here.
Well, I feel like I really stepped out on a limb with this post. I know I may have gone in a different direction from what some of my readers would feel more comfortable with. But as I said, this is a style blog. If my suggestions don’t resonate with you, toss them. And if these tips won’t keep your feet or ankles warm enough, do what works for you. But if style is what you’re after, I think wearing your socks as an accessory is key.
I’ve created shopping widgets with socks and shoes that I’ve mentioned in today’s post. These links as well as the links above in the copy and captions are affiliate links. If you shop through them, I potentially earn a commission on your purchases, but at no added cost to you. Thank you for supporting the work I do here by shopping my links. I appreciate you.
Shoes to Wear with Socks (or without)
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Blessed for My Day
Ninety-nine percent of what we worry about happening never happens. Well, I just made those percentages up. But wouldn’t you agree that most of what we fret over never materializes? Why, then, do we spend so much time assuming the worst, planning for the “inevitable,” working through worst case scenarios and losing sleep over imagined problems? I think much of our woeful anxiety is a defense mechanism, preparing ourselves for the worst so that we can better handle the not so bad.
But a better plan yet would be to trust in the character of the God who loves us. We don’t have to be eternal optimists or look at the world through rose-colored glasses. Instead we can thoughtfully and faithfully put our trust in a God who cares for His children, provides everything we need, consistently treats us tenderly and has the power to override any harm that threatens to derail His plans for us. Let’s trust that God can and will indeed “do far more abundantly than all that we ask or think, according to the power at work within us.” (Ephesians 3:20)
And Israel said to Joseph, “I never expected to see your face; and behold, God has let me see your offspring also.” ~ Genesis 48:11