What Shoes Does One Wear with Barrel Jeans in the Winter?

I was slow to the barrel jean trend. I felt it a passing fancy, and the old style rules ingrained in me since I was little made me worry they were “unflattering.” But barrel jeans grew on me, I think because they do break so many style rules. They're jeans for those who have fewer f*cks to give but still give a sh*t, being stylish but comfortable, relaxed but not lazy. But now that the weather is colder, what shoes does one wear with barrel jeans in the winter?

What Shoes Does One Wear with Barrel Jeans in the Winter?

Here are my suggestions for us grown-ass women who want to have fun with fashion while also being comfortable and practical.

A Sleek Sneaker

A chunky sneaker with the volume of a barrel jean is just too much volume on the bottom half and will create a strange optical illusion. However, the trend right now is for a sleek low-profile sneaker that is retro-inspired, and they look great with barrel jeans!

I personally own the Adidas SL 72 (actually this one, but it's sold out in many sizes) and the Adidas Grand Court Lo and wear both happily with my barrel jeans. I even am able to fit my favorite arch support insoles in my SL 72s. Other options are the Adidas Tokyo, Nike Cortez, Nike Air Superfly, Vans Super Lowpro, Puma Speedcat, and the New Balance 471. The high-top Converse Chuck Taylor sneaker is also a great choice if you lace it up snug.

A Sleek Loafer

Your trusty lug sole loafers are great with wide leg jeans, but when it comes to barrel jeans, you need something lower profile. A sleek loafer is a great option and a way to rock some cozy socks at the same time. Right now, the traditional penny loafer with a pinched or pleated toe is very on trend, but it's also classic enough to stay in your closet for years. I'd go with black or dark brown soft but glossy leather or else go super bold with a unique color and/or finish.

A few styles that I like are the Eastland Classic II which comes in widths, the highly-rated Ani loafer from Reformation, the Tory Burch classic penny loafer, the Margaux “Marlowe” which also comes in widths, and the Cole Haan “Stassi” loafer.

A Fitted Boot

Boots are a winter classic, but there's a good chance the black boots in your closet look awkward with your barrel jeans. What is causing the awkwardness is the shaft. The key to a boot working with barrel jeans is the ankle and shaft is slim and fitted and high enough that the top stays hidden under the pant hem, even when you cross your legs. The fit of the shaft matters more than the heel height or thickness of the sole.

Sock boots and stretch boots are a great option to ensure you get a trim fit with comfort and shaft height. The Regina Pro from Vivaia is a great option that is comfortable, versatile enough to also look cute with all your other jeans and pants, and is water-repellent making them practical for winter slush. The Aquatalia “Stassi” is another great waterproof option. The Ciel Glove ankle boot from Madewell is another great option if you want a suede look. And Reformation has some chic stretch and sock boots such as the “Louie” sock boot and the “Remy” stretch boot.

IMO, the shorter the heel, the longer the toebox when it comes to styling boots with barrel jeans. An elongated toebox will balance out the pant volume and silhouette.

What Socks to Wear with Barrel Jeans?

We grown-ass women are very comfortable with no-show socks. We've had it ingrained in us that socks were dorky. But bare ankles can get cold in the fall and winter, and socks are back in fashion. Go ahead and wear your no-show socks if that makes you comfortable, but if you want some warmth, look for a fitted sock that is tall enough to go up under the hem of the barrel jean and stay there without sagging.

For sneakers, that would be an athletic crew sock, and I encourage you to step away from the white and go with black or a color. The black will recess and let the jeans and shoe take the spotlight, and will feel more modern. You can also do a fu pop of color or pull in a color from your top, or pick the same color as your sneaker to keep things sleek. Personally, I have and like the Bombas Half Calf which come in sizes and the ankles are logo-free.

For loafers, you want a dressier fabric. Trouser socks are better than bare legs, but some may want even more warmth. Again, I have a few from Bombas: the pointelle and the open rib stay up without suffocating my lower legs and look cool. Darn Tough makes excellent wool socks that come in sizes and keep their shape; these are pretty and cozy. Unbound Merino has a really nice solid colored sock; the black is a safe bet. I'd go with black with black loafers, and for other colors either choose something the same color or similar color but darker than the shoe or go with a fun pop of color.