Fall/Winter
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The Best Socks To Wear With Booties in the Winter

I get asked all the time what socks to wear with booties in the winter, so I wrote a post about it!

I know, it’s a conundrum. And let’s face it, ankle boots often look best with no socks, especially when wearing jeans that show a bit of skin.

But that’s not always practical, and I would never suggest you eschew socks for the sake of fashion, even though personally, I’m lazy and only wear them when it gets really cold.

Of course, some booties simply do not look good with socks — those with split shafts, mainly — and those I simply do not wear on the coldest of days.

These are a good example of booties I would not wear with socks.

But most booties can accommodate socks, and it’s fine if they show, as long as they work with the rest of the outfit. In fact, sometimes they add another element of interest that can really make the look.

Here I’m wearing AG Farrah ankle skinnies (they have a 28″ inseam) with Marc Fisher Yale Chelsea boots.

Marc Fisher Yale Chelsea Boots

On top, I’m wearing a chunky turtleneck, and I accessorized with a Victoria Emerson boho cuff.

This turtleneck is perfect for those who want a cozy sweater and can’t tolerate wool — the fabric is 55% cotton, 23% recycled polyester, 22% polyester. It’s cut generously, but I would still say it runs true to size; I have the small.

FYI, both Banana Republic and Victoria Emerson have extended their Cyber Monday sales, so this sweater is 50% off plus an additional 10% off with code BRCYBER, and the boho cuff is 50% off (no code needed.) Also, my boots are 20% off at Nordstrom, and the jeans are $50 off at Saks.

But back to the socks… Oh, they’re 20% off too! Gotta love it when Black Friday sales overflow into the next week!

I usually wear solid color socks that blend into my outfit, so if they show, they don’t really distract from the look. And sometimes, that’s the best way to go.

But I recently purchased these Smartwool popcorn polka dot crew socks to wear with my neutral looks when I want to add a little pop of pattern to the look. I picked up the black and the grey, and I’m wearing the black with this outfit.

These socks are currently 20% off at Backcountry; and you can also find them on Zappo’s, Nordstrom, Amazon, and Smartwool.com.

Not only do they add a fun pattern and texture to the look, but they’re Smartwool, so of course they are very warm.

FOUND: The Best Socks To Wear With Booties in the Winter!

Obviously, you can’t see them when I’m standing up, but when I sit down and move around, they do show, and I think the glimpse of pattern is really fun.

Of course, they also make solid colors for the times when you don’t want your socks to make a statement.

I have to say, from a girl who rarely wears socks, I was loving how cozy and warm my feet felt the day I wore this outfit. I may actually be a convert to wearing socks as a default from now on!

Eh… probably not. I’m far too lazy for that. But when I do need to keep my feet warm, Smartwool socks are going to be the some of the ones I reach for.

Jo-Lynne Shane wearing monochromatic outfit with Marc Fisher Yale Chelsea Boots

Shop the Post:

BR turtleneck (50%  off + add’l 10%) // AG jeans ($50 off) // Smartwool socks (20% off) // Marc Fisher boots (20% off) // Victoria Emerson bracelet c/o // Lagos earrings

Shop More Smartwool Socks to Wear with Booties:

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The Best Socks To Wear With Booties in the Winter

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photos: Alison Cornell

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36 thoughts on “The Best Socks To Wear With Booties in the Winter

  1. It really is a dilemma I have struggled with for years 🙂 There is money to be made when someone finally makes low or no show socks to match all of the booties. I have navy and burgundy booties I love wearing but the sock issue makes it almost impossible. I have found some socks that match but they are WAY to tall (so I actually cut them, but then sometimes they slide down). A running type sock would be perfect in all the colors of booties. Cognac and tan booties are super hard to find socks to match (that don’t show). I wish I could do “no socks’ but I usually get some sort of weird blister on my toes or something; therefore, I just need a sock. These socks you are showing are cute when you want to show your sock, but sometimes you just don’t want to……I hope a sock maker is reading this 🙂 Have a great week !

  2. Sheec socks also now have a fleece one esp for wearing with booties…..i think they might be sold out currently but still i wear those types of socks with my booties – prefer to have “something” even if they don’t keep me warm

  3. I’m glad you wrote this.  I suffer from
    Knowing what socks to wear with slip-on sneakers and booties.  I swear I never have EXACTLY what I need!!  Sometimes I resort back to the old fashioned knee hi hose. Just cuz I don’t know what else to do. 

  4. Sorry to hear about your neck and shoulder issues. You might want to check into having an ergonomic eval of your workplace. This could entail making some minor adjustments in your work station…, such as a lower seating position or keyboard placement or even a few exercises to help you. Take care and thanks for the great sale information!

    1. Thanks, Suzanne, I have never heard of that. We’ve tried to make it as good as possible, and I do have a desk I can adjust to stand or sit, but we may not be doing something right.

  5. I live in the freezing tundra, so I wear socks with my boots and booties pretty religiously. I’ve found that “matching” my socks to my pants helps create a clean line. If I wear black pants, I wear black socks. Light or medium heathered blue socks are great for jeans — they’re hard to find though. Navy for really dark jeans.

    Now, if anyone can tell me how to get their socks to stay up all day … there’s the kicker.

    1. Yes, that is usually what I do too. But sometimes a pattern is fun. 🙂 Have you tried knee socks? My husband swears by them. They look dorky but they stay up – and provide some extra warmth too. I included a couple pairs in my shopping widget.

  6. Thank you for this post.  I for one am a sock wearer.  I just can’t stand the feeling of sticky sweaty feet in shoes without a sock.

  7. I’ve tried wearing no socks with booties, but inevitably my feet sweat and start chafing inside the boot and then I get blisters. No bueno. So I wear no show liner socks from Zella. They are so low they barely cover the side of your foot and they’re not “warm”, but they do cover the toes and heel, so you have something between your feet and the shoe. I can wear these socks under the Vince Camuto Gigietta and Grandina booties and the Jeffrey Campbell snakeskin bootie with no problem, and nothing shows. However, I tend not to wear those booties in the dead of winter when it’s 20 degrees outside. The Smartwool socks look really cozy, I’ll have to check those out!

    1. Yeah, I feel like those boots just aren’t intended for very cold weather. But I have those Zella socks of which you speak – I will try them out of curiosity, but I’ve never found a pair that doesn’t slide down – even the ones people swear don’t for them. Maybe it’s something about my feet? I have narrow heels.

      I’m usually just more comfortable without socks. I prefer the way my shoes feel that way, most of my shoes are good quality and comfortable inside, but I do know what you mean about the blisters. That happens sometimes when I wear them for hours at a time, so it would be nice to have a sock that doesn’t show for those times.

  8. Love the AG jeans in that color. I don’t need more jeans, but I may have to order those. And I order the popcorn socks in the cable version. I needed new socks and I love Smartwool. I’ve stopped buying inexpensive socks. I’d rather have fewer pairs of nice ones. I like Smartwood and Darn Tough wool socks and wear them year-round. Darn Tough makes some great summer socks for sneakers or hiking boots.
    Great idea for a post!

  9. The Sheec socks that Cindy Spivey recommends work great with lower shaft boots/shoes and even flats! Due to a medical condition, my hands and feet are quite cold. I did not believe that socks that do not cover the whole foot would keep my feet warm – but surprise, they do! The socks have technology that keep them on your foot. Highly recommend.

  10. Sharon. I was thinking the same thing about the Sheec sock. I have the regular ones but forgot the blogger Cyndi Spivey mentioned they had the fleece ones. I had planned to grab a pair to try during their sale. But now you say they are sold out. I believe Cyndi always has a discount code for them but it is less than the Black Friday one was. Not sure how I let that purchase pass me up. They are the best no show sock I’ve tried. Rarely have I had them slip down. Cyndi said they never do so could be just me. Highly recommend as they have many styles to accommodate all types shoes. Even heel pumps. Great post Jo-Lynne. I love smart wool socks. It really is just trial and error depending on the jean, boots and weather how to style socks. Love the ones you styled. REI carries lots of smart wool ones too. 

  11. Would you believe that I have on my first pair of Smartwool bootie socks today, that I ordered from either Lands End or LLBean!  Mine do not coordinate with my outfit, so I rolled it down a bit to keep it from showing.  I agree with how good they feel on.  I hope that you will take frequent breaks and change positions while working on your computer.  Have a great day!

  12. We must be on the same wavelength today. I had an early appointment this morning and the weather had dropped to 22 degrees. I wore some cute snowflake black wool socks I had purchased at Eddie Bauer maybe 5-6 years ago. I put them on with my black booties and they don’t really show except when sitting down, then you see just a little. They matched my Halogen ponte pant and were cute when they did show, so I went like that and my feet were warm. 

  13. Hi there! I have a sock suggestion for booties. I like to “borrow” my daughter’s Vans Classic No Show Socks. They are as a thick as athletic socks so they keep my feet warm even though my ankles are showing and they don’t pop off the backs of my heels like the normal thin no-show socks I wear with flats. Also, unlike normal athletic socks, they don’t show around the top of the foot/ankle. It’s a win-win all around! They are also great for slip on-sneakers since that is what they are designed for… Happy Holidays! 😃

  14. I throw fashion out the window in Ohio during the winter. I usually wear my warmest socks with my booties. I’ll wear a slouchy sock if I’m dressing casual. If I’m dressing up, I’ll wear flared or straight jean that will cover my bootie and wear warm socks even if they don’t match.

  15. I’m one of those that doesn’t like socks at all in the warmer months.  I wear my sneakers and slip on sneakers without them.  But it’s too cold here in the winter to go without, so I embrace my socks when the weather turns.  I do love a cute pattern and figure if I have to wear socks, they might as well be fun!  I try to do like you do and match the color so they blend in a bit if they show.  Those popcorn socks are super cute!  Hoping you are able to figure out your shoulder issues.  No fun!

  16. Jolynne,

      Thank you for this post!  I never see Smartwool socks on sale so I loaded up from the Backcountry site. 
      I agree with suggestion for an ergonomic assessment of your workspace.  I had one done years ago by my employer (also have shoulder, neck and low back issues).  One thing that really helped was getting rid of the conventional mouse and going to a roller mouse bar.  It sits in front of your keyboard and keeps your hands in front of you and not reaching out to use the conventional mouse.  My employer bought me the roller mouse and an ergonomic keyboard and I bought them for myself to use at my home workstation. So glad I did since i’ve been home working since March.  Here’s a link to the roller mouse. Contour Design Rollermouse PRO3 https://www.amazon.com/dp/B01MTEH6WZ/ref=cm_sw_r_cp_api_fabc_N9NXFbY1GBYNZ
    Not sure if you have a standing desk but i have an electric one from Uplift Desk and love it!!
    Praying you get relief from the Chiro visits-they are always helpful to me. 

  17. I love Smartwool socks. Also tried the Wit & Wisdom Ab-Solution jeans you wore in a previous post. Love them!!!!! Stay warm❄️❄️❄️❄️

  18. Bombas makes a no-show sock that stays on the foot. You can get them in cotton or merino wool. The merino is quite warm.

  19. What do you put in your booties or tennis shoes that you don’t wear socks with to keep them from smelling? 

    1. Nothing. I don’t have any issues with that, that I’m aware of anyway… ha! No, really, after I got this comment, I took my sneakers off (my bare feet) and sniffed. They’re fine, I guess that’s something that some deal with more than others? I like Leigh’s idea of the essential oil.

  20. Smartwool socks are a favorite at our house. My daughter always gets a pair in her stocking! I wear their thin ankle socks year round with my sneakers for walking. The wool is breathable, moisture wicking and I like it better than cotton. 

  21. I love smartwool socks and live in them in the winter!

    As for your desk, I agree on the ergonomic assessment, but a better office chair could potentially help too. My dad worked on office chair designs at Herman Miller, so I’ve picked up quite a bit on ergonomics over the year. Herman Miller offers a great variety of chairs focused on how the body should be supported and move while seated. You can find more on their website or Design Within Reach. I hope you shoulder feels better soon!

    1. Funny! I have a Herman Miller chair. I got it when my hip was all messed up last year. So I have that covered. I got the standing desk then too. I feel like I should be in good shape, but alas…🤪

      I do appreciate the info though. They do make a really nice chair!

  22. Paula-

    Your question re: what to put in shoes to stop the smell…I put a few drops of lavender essential oil on a cotton ball and rub it on the inside of the shoe, or rub it on the bottom of my foot before I slide it into the shoe. I NEVER have smelly feet!

  23. Living with Michigan winters, I wear flesh colored fleece lined tights with my low profile booties to extend their seasonal wear. They are not too noticeable, and they keep my entire lower body a bit warmer. Amazon has many options, and to me, thicker isn’t better for my usage underneath.

  24. This is one of those “I beg to differ” comments. I have no idea who the heck started the “socks must never show” idea but they lived where it is WARM. No, boots do not look “better” without socks….this is just one option and boots look just fine with socks. It is a matter of preference and weather. Time to stop being a slave to a passing fashion idea and go with what you like as personal preference and in many cases what keeps you warm and frost-bite free.

    1. I resent being told I’m a slave to fashion. This is a fashion blog, and we discuss matters of fashion, and yes, some styles of boots do look better without socks. Of course people should do whatever they please, but this post is about answering a fashion question I get all the time, and people can do what they want with the information, but there is no need to be rude.

  25. Oh, the sock conundrum! 😜 I do not like wearing socks, and like you, I avoid if I can. It seems that everyone I know is a sock lover, so I’m glad to know there is another person who eschews socks unless necessary. 😂😂

  26. Years ago I had neck arm shoulder issues. The ergo evaluator suggested I learn how to mouse left-handed using an upright mouse. Upright mouse means your hand is hel like a handshake when using and its more natural without the death grip. Both ideas solved both issues! I mouse left at work, right from home (lite use). Amazing. I still do this even WFH. Hope you feel better!!!

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