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!
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.
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?
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.
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.
Shop Socks to Wear with Sneakers:
Stay In Touch
If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.
I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a friendly place to discuss all matters of fashion and style with other women, share your outfits, get advice, and stay up to date on all the happenings in our community.
This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!
photos: Alison Cornell