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How to Wear Socks with Pants Stylishly this Winter

January 17, 2023

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.

How to Wear Sock with Pants 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.

Wrong Shoes
loafers // similar socks

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.

Wear White Socks for Impact

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.

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. As we age our ankles sometimes get a little thicker, so this seemingly small style choice can make a significant difference in appearance.

How to Wear Socks with Pants in Winter and Look Stylish

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.

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 // belt // similar loafers (more economical) // similar socks

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 loafersmore 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.

How to Wear Sock with Pants this Winter
similar loafers (more economical) // cashmere blend trouser socks // pants

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.

Wear White Socks
trousers // belt // similar loafers (more economical) // similar socks

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.

Wear White Socks

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.

Red and Camel Outfit with Socks and Loafers

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.

Matching Your Socks to Your Trousers

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.

How to Wear Sock with Pants in the Winter

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.

Socks Included

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.

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

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.

How NOT to Wear Socks with Pants this Winter

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.

How to Wear Socks with Pants in Winter

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:

Secret 3.0 Lowcut socks

And yes, these socks really do stay in place with wear, at least on my feet.

Secret 3.0 Lowcut socks

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

xoxo, Kay
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72 thoughts on “How to Wear Socks with Pants 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……

    1. Such a great post! I needed this after recently moving to New England from So. California. I had pretty much forgotten that wearing socks is a thing during the winter. I have been going by the rule of matching socks to pants or shoes. I checked out your Pinterest board and can see how much more attractive these outfits are wearing socks as an accessory. I particularly love the look of the white socks and black loafers! Thank you Kay!

  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.

  33. I follow a couple of amazing women on IG who may be a tad bolder than the usual women over 50, and they rock some print socks. Because it’s as you say, if you’re going to have socks be shown, then make it look intentional.
    I’ve also loved seeing fun socks peeking out of ankle boots over skinny jeans.
    I applaud you for having fun with this category.

    1. Jodie, well said, and another great point to add to this morning’s great blog. “Intentional” is the key word. I have been “bookending” my outfits with stylish coloured socks for years. In the cooler seasons, comfort and practicality are key, but an intentional pop of colour in my socks adds interest and a subtle but clear indication that I have confidence in my personal style choices.

  34. I have never given this much thought butI totally see what you’re saying! And I especially love your Pinterest board showing how socks added to the style!!!

  35. Hi Kay! I am certainly an intentional sock gal! I love wearing fair isle or argyle or striped socks that show with my low cut booties or loafers or…wait for it…my Birkenstock sandals!! I see that alot in the younger set and it gives me more chances to wear my sandals. Of course this would happen in a very casual setting! I wear them with ankle jeans or rolled up/cuffed boyfriend jeans. Thanks for all your research on the topic. Love the examples on your Pinterest page. 🙌

  36. I also love this post, Kay. I’m mostly a wearer of boots in my northeast Ohio winters, but it’s nice to know how to wear socks if they’re going to show. Thank you! Also, love your hair in the photos with the camel sweater…always love what you do with your hair, but the camel style I haven’t seen before. Very becoming.

  37. I think you have a cool factor lol but I know what you mean. I too feel like I don’t have the cool factor either but I really enjoyed your post on the socks. I did learn some tips though most of them are you do on all ready. Nice to know I am right Most of the time. I also believe the way you do and we always have to trust in the Lord.
    I am really enjoying the Bible verse Memorization that some of us ladies are doing.

  38. WOW! I guess I’m really out of the loop on how to wear socks. I was always told to match my socks either to my shoes or my pants. And certainly, NEVER white socks with black pants; a complete fashion faux pas . LOL. OK. That was in the 1960’s, 70’s 80’s, 90’s and…….? I need to update my “sock” look when wearing pants. Now, dashing off to check out my sock drawer!

  39. LOL, I’m ‘sock challenged’! I remember your similar post last year and have tried to up my sock game, but I find it rather difficult to get a stylish look for myself when my socks are going to show that doesn’t stand out in a garish way, sending the eye straight to my ankles….not exactly my focal point goal. 😉 I totally agree about NOT wearing socks with ballet flats. That just doesn’t work. And if the socks aren’t going to show, then they can match. I’m okay on that. But bookending socks? I’m gonna work on that. Thanks for your ideas. I love your blog!

  40. I like the splash of color you have chosen for the socks in the photos. I tried this a week or two ago and really enjoyed it, much to my surprise.

    I’m looking for a truly nude, but not fragile pantyhose. Any suggestions?

  41. Lol, loved this! I hate cold damp feet in The winter and live in north east Ohio. My different opinion is I love cute socks and wear all kinds of patterns and let them shine! I get so many comments and other ladies laugh with me about the crazy socks I wear. I’m 68 and have always loved socks that express my mood. Today I wore sock monkeys. I sure say I’m very conservative in clothing choices for the rest of my body, lol. Thank you Kay!

  42. Great insight! I think we all have had a bit of the “what is in fashion” queries when it comes to socks/ shoes in winter. Thank you for bringing a bit of light to the subject. Still unsure on the white sock as a contrast, though. A bit “Michael Jackson”? ☺️

  43. socks with driving mocs? Loved!!! this post- so helpful. I have always had sock creep where the back goes down and into my shoes- high arch- any idea why or do you know of socks that will not creep??

    Thanks so much! I am referring to socks which are above the ankle- thanks again@!!

  44. Well, you did go out on a limb with this post and good for you for having that courage, I loved this post. I don’t feel comfortable in a bootie; I just don’t like the way they feel on my ankles. So I wear loafers so much in the winter, so your tips work for me. Thank you Kay.

  45. I would never have thought that I can actually w wear socks with certain shoes. But you provided some great looks and even better advice on how to do it and still look fashionable. Thank you!

  46. I’m a baby when it’s cold so I wear socks a lot. Unfortunately, I haven’t been please with how my socks and loafers looked, so taking your suggestion and remembering I used to have fun with my socks I’m going to up my sock game. I found light gray socks pair nicely and give a good contrast to outfits.

  47. Thank you!!! I am a woman of a certain age who has been trying to figure out how to keep my feet warm (in OH well) and have some style for what seems like forever. Generally, I give up and default to boots. I have a good sense of what shoes look good with socks. But after that, I was at a loss. I couldn’t find any “rules,” and looking at photos wasn’t giving me what I needed; they were mostly too runway-esque or “boho” (a la Birkenstocks and chunky wool socks). Your guidelines filled in my style gap perfectly. This might seem like a long comment about socks, but let me tell you, the struggle is real! Thanks again. Now pardon me while I go sock shopping!

  48. Is there a time or place for knee-high hose with pants in 2023? I have a pair of black smoking loafers that I’d like to wear with some black jeans and wondered if that would the right “socks” to wear. The loafers are definitely not “male” inspired. Thin soles.