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How to Wear Socks Stylishly this Winter

January 25, 2021

Got style? Got cold feet? I hear you! It’s a conundrum I didn’t take seriously until I moved to Ohio a year and a half 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 little research, a lot of thinking and a bit of experimentation, and I think 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 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 56 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 fishnet hose either. So as we brooch 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. 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.

Choose Shoes Wisely
loafers // similar socks

In my research I noticed that I never once saw someone wearing socks with ballet flats and calling it stylish. 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.)

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. There’s a big difference.

Tassel Loafers
loafers // socks // ponte knit pants (similar)

Besides boots that have a shaft that fits under my pants, I only wear socks with my penny loafers and tassel loafers. 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. Look for more shoe options in the shopping widget at the bottom of the post.

Again, if your goal is style, I wouldn’t wear socks with ballet slippers, pointy toe 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.

Consider Your Pants Choice When Wearing Socks
trousers // similar sweater // belt // loafers // similar socks // red crossbody // earrings

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.

Consider Your Pants Choice When Wearing Socks
loafers // socks // ponte knit pants (similar) // sweater // fitbit // fitbit band // necklace // earrings // similar satchel

Wear Your Socks Like 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.

When your socks are hidden, wear them as undergarments and choose socks that match your pants and blend in.

But when your socks are exposed, wear them as an accessory and choose a color that will add interest and 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!

Wear White Socks for Impact
trousers // similar sweater // belt // loafers // similar socks // red crossbody // earrings

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.

Check it Out! I’ve created a Pinterest Board with all 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.

#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.

Wear White Socks
trousers // similar sweater // belt // loafers // similar socks // red crossbody // earrings

Here’s another similar look in a mirror selfie. Here I did choose off white socks to coordinate with the off white sweater I’m wearing, but the contrast is the same.

Wear White Socks
fleece lined cargo pants // similar socks // loafers // similar sweater // necklace // earrings

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

I did this above with ivory socks to match my ivory sweater. But let’s see how I also bookended another look. Below I bookended the outfit by wearing a rose colored sweater and socks in a similar hue (another option). I wore my Paul Green python print loafers, which are 44% off at Nordstrom Rack.

Bookend Your Look by Repeating the Top Color
loafers // socks // ponte knit pants (similar) // sweater // fitbit // fitbit band // necklace // earrings // similar satchel

I’ll have to illustrate further with a few mirror selfies. We ran out of time taking photos the other day when we got called to go see a house (we’re house-hunting!). But I want you to see that these formulas work with other outfits, too.

loafers // socks // ponte knit pants (similar) // sweater // fitbit // fitbit band

In the photo below I’m wearing my brown pintuck pants from Athleta bookended with this blue crewneck sweater and baby blue socks. (By the way, Athleta calls this sweater “voyage grey,” but it definitely reads light blue to me.)

brown pintuck pants // crewneck sweater // Paul Green loafers // socks

Here’s a close up view of the socks and loafers.

loafers // socks // ponte knit pants (similar)

And you absolutely can bookend a look with coordinating socks when you wear jeans, too. I just didn’t get any photos of that. Maybe I’ll add them later. I’ll definitely shoot a look with jeans soon. Meanwhile, let’s move on to the third style formula.

#3 – Add a Surprising Splash of Color

Whether you add a bold splash of red, as I did in the outfit I wore last week, or a more subtle swath of gold or green, you’ll definitely be making a style statement with this formula. Here’s the actual outfit I wore Thursday evening. It made me so happy!

Socks Included
loafers // jeans (no longer available) // similar socks // similar sweater // belt // earrings

I’m loving those red socks! They’re Lauren by Ralph Lauren and I got them at Macy’s in a multi pack similar to these. Unfortunately I can’t find them online. But these would work great, too.

Here’s a similar look with black jeans, a black sweater, black loafers and gold socks. Again, my gold socks are from J.Crew, but they’re not available online. These or these would sub in well.

How to Wear Socks
loafers // jeans (no longer available) // similar socks // similar sweater

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. But if you want to wear something besides a solid, I think something like these tie-dye socks can work. Again, mine are no longer available (I purchased them in Nordstrom), but these are similar. Other prints that might wear stylishly would include stripes or animal print.

How to Wear Socks Contrast (2)
jeans // similar socks // loafers // sweater

Since the quality of the photo is so poor, let me explain that the tie-dye socks are light to dark blues and greens. So I think they coordinate well with the blue jeans and blue sweater, while adding a little whimsy. But they still look on trend. Whereas socks with flowers and kittens and hearts can look a little silly on a grown woman. Look, I have those, too. But I wear them at home or under boots.

Below I’ve taken two shots so you can see the difference between wearing colored socks and wearing socks that match your pants or jeans. Do the matching socks work? Yeah, they’re okay. But to me the navy socks look Iike I’m trying to hide them. Whereas the red socks look like I’ve made an intentional style choice. And remember, intentionality computes as “pulled together” and chic.

How to Wear Socks Contrast
Calla Maggie Loafers (use code KAY20 for 20% off your order) // jeans // similar socks // sweater // necklace // earrings

So I would definitely choose to wear the look on the right over the one on the left. It’s more fashion forward and looks intentional and confident. Again, I think the key is wearing your visible socks as fashion accessories rather than undergarments. On the left, I did extend the legs of the jeans so that the sock isn’t showing as much. But on the right I wanted my red socks to be seen even more, so I cuffed these boyfriend jeans a little.

Don’t forget to check out my Pinterest board on Wearing Socks in Winter if you’d like a little more inspiration. And follow me on Pinterest while you’re there!

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.

How to Wear Socks Stylishly this Winter

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

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xoxo, Kay
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49 thoughts on “How to Wear Socks Stylishly this Winter

  1. Obviously we should do what we like, but I feel wearing lighter socks with a dark pant draws your attention away from your face and straight to your feet. For me, it also doesn’t look young and stylish but more matronly. In order to elongate the legs and keep the eyes up towards your face, I keep my socks the same or as close to the color of the pants and shoes. I also think the pants should have a longer inseam when wearing them in winter with flats as that will also keep your ankles warmer. I think ankle pants should be more of a spring, summer, and/or fall pant unless being worn with a boot with a certain shaft height. IMHO 🙂

  2. LOVE this post Kay!! You put wearing socks into perspective and that we CAN wear them to keep our feet and ankles warm as well as stylish!! This has been a problem for me for YEARS. My feet and ankles get so cold in the winter but I was afraid to wear socks for fear I’d look like some old woman! Ha! Well, I am old (80) but at least now I know I can wear socks ‘stylishly’, thanks to you!!

    I have fretted over my socks for years, always wondering if they looked right or wrong. Kay, you clarified the “sock situation “ for me in this post! Thank you!

  4. Thanks, Kay, for much thought and research. You put much time and effort into all the picture options. The photos are helpful to illustrate the ideas. You have made me rethink socks. Great info.

  5. One of many things I love about your Blog is that you touch on topics I’ve not seen addressed in other style blogs. I see all the fun colorful socks in the stores and wonder how to wear them other than hiding them under boots, and then that seems like a waste of good money when basic neutrals are often cheaper. I never thought of wearing socks as an accessory. You are onto something here and have found fun ways to keep cold feet warm yet stylish! Men have been having a moment with fun, colorful, and sometimes whimsy socks for several years, it’s time us gals give them a run for their money! LOL

  6. Good Morning Kay and Happy Monday,
    Love this post. You have rocked my world. I am so thrilled to be able to wear socks again with my penny loafers and jeans. It is so cold in Michigan right now and there are days when it is dry. I sometimes don’t want to wear boots. Wearing knee high nylons are not that warm. So, I will be excited to go through my sock drawer and see what I have to match with my outfits. Have a blessed week.

  7. Your BFMD is so timely. This afternoon is my home inspection (I’m the seller) and I’ve been more or less a wreck. I’ve been praying through my stress and trying to trust God as I know I can. Your words really hit home and I’m so glad I saw this.

    I enjoyed your tips for socks. I look for beautiful socks and have found good ones in gift shops on the compression sock racks. I wear them as accessories!

  8. Kay, you shared some really great tips and opened my eyes to what is on trend. Yes, you took a different path than what I was expecting, but I enjoyed your path. Thank you for spending time doing the research! You look so confident in your pictures! Great BFMD. I hope that you have an awesome day.

  9. Thanks Kay for clearing this up. Every time I open my sock drawer, I ask myself , “What color?” I always wear socks in the winter to keep my feet warm, but I also want to be in style. Look forward to your tips for keeping me in style.

  10. WOW! I had always been matching my socks to my pants but now I feel more confident trying different colors as accessories! I have to admit that I smiled at your beginning comments about goals and shoes! Very cute and well said.

  11. This is a great post, and I’m impressed how nice these socks look, I would never have thought that.

  12. What about sneakers? I have suede for winter. Of course I have sneaker socks, but my pale, veiny, and COLD ankles are not at all attractive.

    1. Hi Mary. You can wear your sneakers the same way I’ve described here. It turns out sneakers are really a variation of the Oxford. And they are shoes with which you could traditionally wear socks, so there’s that too. However, I would make sure you’re wearing fashionable sneakers as opposed to running shoes (and it sounds like yours are fashion sneakers). And thicker socks would probably look good, too. However, there is one caveat. You’re going to have to take into consideration the color of your sneakers, too. Probably just need to play around with looks a little. ?

  13. Love this post! Lots of great, useful info. All the Dressed For My Day readers should band together and see if we can start a trend of looking stylish in socks 🙂

  14. Good Morning Kay!
    Loving your post today on socks! Socks have always been a dilemma for me . Your post cleared up so may questions. I love your ideas of matching sweaters with socks . Also what shoes to wear with socks was a great tip too! I am going to buy some new socks!!!!

  15. I liked this post but I am short and a little wider than I should be, so I wear socks that are close to the color of my pants when I go out. At home, I like to match them to my top for fun. I love your fashion tips but have to adapt to my own stature. Most of these clothes are way beyond my budget but I look for more budget friendly options. . I especially like the spiritual section of your blogs and videos. Thank you. May God continue to bless you.

  16. Good morning Kay! My first thought was… I really like your hair! It looks full with a blunt trim. AND yes on the socks! My husband has been having all the fun in that department for a few years. I do have a question though. When you sit down and maybe cross your legs, do you want just socks to show, or can skin show? (Back to Pinterest 😉

    1. Hi Annette. If you looked at my Pinterest board you probably know the answer to your question by now. It looks quite stylish for your skin to show when you sit or even when you’re standing. I didn’t mention it because most of my readers who requested this post were looking for warmth. But if that’s not so much a factor, then scrunching the socks down or turning them down is actually quite stylish. ?

  17. Hi Kay .. you ‘knocked my socks off (or I should say ‘on’) with this post. I loved it & especially the bookend approach. Question .. do you think this would work for flared slacks where you’d probably only see the socks a little or when sitting? Also are wearing skin tone hose (or a fun color ala your sock ideas) no longer fashionable under slacks? Thanks!

    1. Hi Frani. I would wear socks under full length flared pants as undergarments, matching them to the pants. Yes, you absolutely can wear skin tone hose or knee hi hose in the same color as the pants.

  18. Great post! Thank you for covering a topic that has stumped me for years. Just because we live somewhere cold doesn’t mean we have to give up on looking nice every winter. God bless and hope you find a great house to become your home.

  19. Keep doing the great job you are doing. Know all the research you go through for your post.
    I loved the tips. I have the rose colored Ashley mohair sweater and loved the idea of the berry
    like colored socks to wear it. Remember years ago when I was in retail that we were to show the
    customer same colored socks as the sweater, etc in the winter and I also had every colored sock
    to go with every outfit.
    Loved your bfmd post as well, as always.

  20. Great blog today! Thank you for bringing clarity to the sock/ shoe issue. Being from Minnesota socks are a no brainer in the winter. That being said, I have found no show smartwool socks. My ankles may be exposed for a short time but my feet are warm! They are a little on the pricey side but cost per wear is pennies. I wear them year round since wool doesn’t absorb moisture. You have challenged me to venture out into the world of statement socks. Off to the store I go……

  21. Great post, Kay! I think socks can always be stylish and complete an outfit. You mentioned cutesy socks like hearts and kittens, but I have worn some cute patterns this winter. One was a tartan plaid, another a leopard print and Scandinavian-inspired fair isle socks. I purposely wanted them to show with lower cut booties and fashion sneakers. Made me smile when I looked down at my feet! Also, I loved the pics of Diane Keaton in your Pinterest page!! Always stylish!!

  22. So FUN!! Thanks, Kay. Are you familiar with the children’s book, “If You Give a Mouse a Cookie?” Well, if I’m going to wear socks, then I will have to get a pair of loafers again!

  23. Even if what we worry might happen does, it never happens the way we think it will. I live by one day at a time as I get older. Never borrow tomorrow’s troubles for today the Bible says. One things for sure, life constantly changes doesn’t it?
    I like socks but I find I like mixing dark neutrals. For instant maroon socks with my brown pants and brown loafers. Low contrast. Navy socks with my grey loafers and grey pants.

  24. Thank you so much for addressing my questions about socks, Kay. As always, you do your homework and deliver such a well-considered response. And thanks for the additional images on your Pinterest board. Shall ponder these new-to-me looks. Of course, if, like me, your shoes aren’t always stylish because you’re going for comfort, then I wouldn’t want to draw that kind of attention to them.
    BTW…white socks w black pants and black shoes…also work if you’re a dancer and want to draw attention to your footwork. “Billy Jean’s not my lover…” 🙂
    And ps. The ads are on the left again today blocking content. I tried drag/dropping them to the right side where they wouldn’t block, but they wouldn’t go. Ad source is…AdChoices…

    1. Ok. What browser are you using? Was it Chrome? I’ll report to AdThrive. But I really still think it may have something to do with your device? Just because no one else has said anything. But AdThrive will definitely want to know. Thanks for letting me know. I’m glad you enjoyed the post. ?

      1. Chrome, I think. Although it could have been Edge. Sorry for the lack of specificity. I did notice that as soon as I closed out of that post and was back on the home page of your website that the ads appeared in their non-interfering places–at the bottom and left of my screen.

  25. Great post. I remember when cropped pants came on the scene. I searched everywhere on the Internet for ideas, but the ideas weren’t there. I wondered how in the world people stood having their ankles exposed. I live in Florida and must have socks in the winter. Ankles and neck covered keep me warm:) You have some great ideas here. I definitely think embracing wearing socks makes it appropriate for winter.

  26. Love this post and I appreciate all the hard work that went into it. Living in Canada socks are a must in winter. Thank you, Kay!

  27. I just don’t like the white socks with the dark pants. My attention goes to the socks. I understand the logic but it doesn’t do anything to elongate the person. I’m always trying to make myself look taller and thinner. Some of the other looks are better. I guess it’s all a matter of preference and if our feet are cold, then we have to wear them!!

  28. Another great post! Thank you for making things more clear. When crops and sneakers came on the scene, things became muddled. I ended up just buying higher shaft booties, black pair & tan pair. But I really miss wearing a low heeled shoe. Thanks for showing me how to do it stylishly!

    1. Loved this post! Lots of great ideas. I’ll definitely be rethinking my sock situation. I love to wear socks and I have plenty to choose from. Lol!
      Thanks for the post!

  29. I love your posts! And appreciate the time you take in researching your topic. What a fun way to keep warm and be stylish.
    Your content is always written so clearly, with humor and great ideas.
    Thanks for this one as well!

  30. Kay, thank you for this post. I looked at some pictures on-line and googled some articles on socks, but I couldn’t pull it together as you have. You answered most of my questions in the article and the rest of them in your answers to readers’ questions. A wonderful, needed post and a wonderful community. Love your BFMD.

  31. Hi Kay, I am in the uk and I can’t do without socks in the winter my husband purchased me some lovely ones with sparkly stars and I love wearing them, thank you for all your helpful tips and advise, I am so glad I found you on Youtube,

  32. I have just recently found your videos and am starting to read your blog posts as well. I am enjoying them a lot. I know this isn’t the question here and maybe you’ve addressed it elsewhere, but can you recommend a no show sock that actually stays up? They often slip off of my heel and end up scrunched in my shoe but I hate to go sockless even in nicer weather. Thanks for your help.