Fall/Winter Fashion

How to Wear Sneakers in the Winter

Wearing sneakers with your street clothes is now a widely acceptable sartorial choice, and I’m a fan! I love it when trends are practical, and I often find myself passing over my boots and loafers in favor of my favorite fashion sneakers.

I’ve had some questions lately about how to wear sneakers in the winter, so let’s discuss!

old Naadam sweater // AGOLDE Riley Long Jean (29) // Veja Esplar (39) // J.Crew Cashmere Blend Crew Socks

This post is actually by reader request:

I would love to wear sneakers with jeans in the winter but it’s too cold without socks! Is it ever ok to wear socks with them? Or what about wearing high top sneakers/shoes (not boots) that would be hidden under straight leg jeans? Would love a post on this.

Great question! First, let’s discuss the best kind of fashion sneaker to wear with jeans in the winter, and then what socks to wear with them.

What Sneakers to Wear with Jeans in the Winter

I usually opt for leather or suede rather than canvas sneakers in the wintertime because they’re warmer, and they hold up better to the elements. My favorites are my Veja Esplar sneakers, followed by the P448 John.

jeans (29) // sneakers (39) // socks

Another good option is a hightop sneaker, although I don’t personally have any. They provide good ankle coverage in messy winter conditions, so that makes them a practical as well as stylish choice. Retro sneakers like the New Balance 237 are also very much on trend right now.

Shop Sneakers for Winter:

What Socks to Wear with Sneakers in the Winter

I almost always wear my sneakers without socks, even in the winter, mainly because I’m lazy, and I like the look. But it’s perfectly acceptable to wear socks with your fashion sneakers, and I notice stylish women doing this more and more these days.

Which begs the question… what kind of socks, and what color?

socks // sneakers // jeans // earrings // watch

The safest bet when it comes to wearing socks with sneakers is to match your socks to your sneakers or your pants. It doesn’t need to be an exact match – it just has to be close. If you don’t have a good match, you can wear something in the same color family.

You can also choose a sock in a contrasting color or a fun print to add a bit of whimsy to your look, if that aligns with your personal style.

photo credit: Free People

I like to keep it simple, so when I was wearing white sneakers with beige accents with light wash blue jeans last week, I grabbed this pair of ivory cashmere trouser socks. They coordinate well with the shoes and don’t create too stark a contrast with the jeans, which aligns well with my style goals. (I define my personal style as current, polished, and understated.)

I picked up these socks when they were on sale at J.Crew during the holidays, and they’re a pretty good price right now, but unfortunately they’re backordered. I have the camel and grey as well, and I highly recommend them. They’re so cozy and soft and warm, and I wear them with everything from booties to sneakers.

I also like to wear them around the house in lieu of slippers. I always bring them when I travel in the winter, to use for that purpose, since they’re much less bulky than slippers.

socks // pants // top // bracelet

Of course, there are plenty of less pricey options out there that would work just as well with sneakers. These Smartwool cable crew socks are another solid choice, and I just ordered this 3-pack from Amazon when I saw another influencer I follow wearing them with sneakers. They also work well with boots.

If you like to have a little more fun with fashion, it’s also very trendy right now to wear chunkier socks and scrunch them a bit.

Tube socks are big right now, too. Also, look at the pictures on the Free People website to see lots of other fun styles and colors, if that’s your thing.

Shop Socks to Wear with Sneakers:

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photos: Alison Cornell

Join the Conversation

29 thoughts on “How to Wear Sneakers in the Winter

  1. Have you seen the Vintage Havana brand of sneakers? I saw them online at TJ Maxx, they are similar style to the ones you wear but with fun accents like gold, leopard, or snake print.

  2. Thesedays, when soooo much of my comfort-level definition of “casual” often leans (probably) 70/30% in favor toward athleisure to begin with (because: leggings are really more forgiving throughout the day than the fit of jeans, for my own body type, feel) — you think adding a “dressy” shoe (typically: ankle boots in anything less than snow for me!) is your one last option to NOT look like a *total* gym rat lol.

    Thank you for showing higher-end sneaker choices for more stylish alternatives. The look of these are a lot better than the canvas white Keds I remember during the ’90s (if you’d wanted a relaxed, actual “shoe” then instead of sandals which didn’t again scream “gym footwear” — though, of course, you wouldn’t go trekking through the muck on the streets for a power walk in something at this price point!).

  3. I purchased a retro pair of Reebok high tops from Amazon, and have been wearing them all winter!!! I love the style and profile of the sneaker. Took me right back to the 80’s!
    I’m considering ordering the lo cut princess style Reebok for the spring.
    I have been wearing socks that match my pants, although with the high top it’s not as important.

    1. Yesss! Back in the day (Eighties): I always went out in black Reebok hi-tops with fuschia slouch “sox” (aaannnddd: black knit stirrup pants with some oversized top full of Espirit or Danskin logos on it, but never the kind with the drawings of cats or hippos in aerobics outfits!).

  4. I think this is a VERY difficult look to pull off while looking like you intended a fashionable look instead of an “I don’t really care what I’m wearing” look. Only the young, wearing the trendiest looks , seem to pull it off when I peruse Pinterest. I’m steering clear of this one.

    1. Annie, you said just what I was thinking. I just can’t get into socks with sneakers. It reminds me of my elderly Aunt wearing her socks with her clunky tennishoes. I don’t like them with the more streamline sneakers either. At my age, I’ll be sitting this out too. Thats whats nice about fashion, you can pick and choose the trends you are going to try and do.

    2. All I can see with this look is the 80s – mom jeans and white sneakers. For me, if I’m old enough to remember the first time around (and I am), then I’m not doing it the second time. 😅

  5. Jo-Lynne, thank you for this post! Your Veja’s have been enticing me to try a pair of sneakers, but I need arch support similar to Birks or Olukai’s for comfort. I am wondering about the support of the Esplars? Have you tried the Campo?

    1. The insole of the Campo slips out, so you can put in a arch support insole. I have custom orthotics that fit nicely in the Campo. The tongue is longer, and from reading I’ve done online, a lot of people leave the top lace hole empty and have the tongue slide over to the side. I found that works great. If you google Campo vs Esplar, there are a few blog reviews out there comparing them in detail. The Esplar just wasn’t cushy enough for me. Hopefully one or the other will work for you.

  6. Hi can you share the watch you are wearing on the cover photo of todays post? its very pretty It has a rectangle face Thank you

  7. I have the Veja V-10 and a couple other pairs of fashion sneakers. I just don’t feel like wearing them in the winter because they don’t feel warm enough. I have a pair of Marc Fisher Chelsea style boots with faux fur trim that I can just slip on with my Mother Insiders and no skin is showing. So they’re perfect for keeping warm while running errands and also looking “wintery”. I’m more likely to bust out the sneakers when it’s in the 50s and warmer.

  8. Your posts have grown to be quite educational. I appreciate the work you do to inform us about various products. You have inspired me to get all kinds of cashmere! I’d love one of your thorough lessons on how to care for different types, brands, and articles of cashmere clothing.

  9. While your trip home was short, it sounds like it was a great visit. I ❤️ socks and just ordered a 3 pack from Amazon in a beige color. I hope you have had a great day!

  10. As a Spanish myself, I’m going to stand up for Spanish fashion here.I have recently bought a new pair of a fantastic Spanish brand which is a must have for fashion insiders all around Europe!!! It’s the HOFF brand.HOFF stands for Hall of fame,and it has two distinctive lines: Cities and Districts all around the world.I have acquired the Hoff Barcelona (Ah-ma-zing)and I use the best sneakers evah:Kiff kiff, which is another fabulous Spanish brand.

  11. Never could understand how anyone could wear sneakers or boots without socks in cold weather! Glad it seems to be ok to do so now.

  12. Hi Jo-Lynne,

    Definitely, sneakers without socks give that special always trendy look. I like when you post how to pair sneakers with basic outfits and pair them with minimalistic sneakers without socks. My daughter has a pair of vejas, and P448s, and pair literally everything with them. And bdy never wear socks.

    Keep it up.

    1. Sneakers without socks is definitely a look, and it’s still relevant, but wearing socks is actually very much on trend at the moment. The trendy way is the thick, chunky tube socks with more athletic sneakers, but I also see very fashion-forward women with more minimalist style wearing the trouser socks with Vejas and Converse as I’m doing here. The key is making it look intentional.

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