As the weather chills and the holidays approach, your wardrobe adapts for winter. Summer styles get put away to make room for cozier, cold-weather-ready pieces.
A key part of winter styling that many people overlook is their footwear. Having the right shoes in your seasonal rotation is essential for building everyday outfits with ease.
Whether you’re searching for yourself or someone else, a timeless pair of sneakers is a must-have for building bundled-up ensembles during the chillier months of the year. Perfect for casual gatherings, last-minute shopping trips, or wowing that special someone as they’re unwrapped, the best shoes blend comfort with classic aesthetics for adaptable wear.
To make selecting a pair of sneakers simpler, we’ve put together this guide of thoughtful winter-ready picks. Full of carefully curated favorites, these are our top casual footwear choices for this holiday season.
All-American Surplus
Winter style is defined by bold color choices. The All-American Surplus Collection places color at the forefront with its sleek, monochrome design.
Available in three confident tones, this refined canvas shoe translates military heritage through an elevated lens. Rich navy, muted olive green, and striking black each take after traditional mid-century uniforms. Understated aesthetics are met with matching laces, stitching, and soles, creating a streamlined appearance perfect for everyday.
Their retro appearance makes them an ideal fit for styling with old-school workwear pieces like chore coats, flannels, and cargo pants. Pair them with tactical-inspired choices, matching tones, or garments with mid-century roots for a distinct winter look.
P.F. Flyers x BEAMS+
If you love exploring the outdoors, your winter footwear will need to keep up. Our limited-edition collaboration with Beams Plus is an exceptional choice for winter adventure.
Reimagining our classic Grounder High-Top, The BEAMS+ Boot innovates our most rugged choice with new military canvas and an improved outsole. Built with deeper lugs for superior traction, it’s grip you can count on as you reach for new heights this season.
Higher mudguards and a gusseted tongue keep feet sheltered from the elements, making them a strong choice for snowy days. Styled with pieces that place performance at the forefront, it’s utilitarian style at its finest.
The 1993 High-Top
It’s our most popular sneaker for a reason. A playful mix of ‘90s nostalgia and practical design, The 1993 Center High-Top is exactly what an everyday shoe should be.
With an all-black color palette, lightweight canvas, and our signature Posture Foundation support, it’s a versatile staple that never goes out of style. This comfortable black casual shoe works with almost any wardrobe, making winter styling a snap.
Plus, wide width options and kids' sizes mean you can match with the whole family.
If you want a sneaker that is sure to impress this season, The 1993 is the shoe for you.
Basecamp Camo
A unique spin on camouflage, The Basecamp Collection brings luxurious camo jacquard to warm, winter-ready tones.
Available in two inviting neutral hues, this sophisticated sneaker can easily be dressed up or down for all occasions. Off-white rubber soles meet soft brown and tan, giving this twist on The Grounder an intentionally distinguished feel.
Practical detailing, like reinforced stitching, heavy-duty soles, and tongue and heel pulls, give it both form and function.
The Grounder Basecamp High-Top can be worn with casual classics, such as henleys and jeans, or paired with more polished pieces for clever cold-weather styling. Traditional choices like chunky cream knitwear, khakis, and leather accessories bring out the shoe’s refined appearance, while high-tech garments like puffer jackets and hiking backpacks highlight the utilitarian design.
Wobbly Waffle
Lastly, what would winter fashion be without a hint of plaid? The Wobbly Waffle version of The All-American High-Top brings this traditional winter print to comfortable cotton through the slowmade art of handweaving.
Crafted carefully by artisans with organically grown fabric, our limited edition collection with Story mfg. beautifully showcases natural streaks of color and rich blue hues. Each strand is dyed by hand using indigo plants. Woven together with raw ecru strands, the result is a uniquely textured waffle pattern.
A true statement sneaker, the variations in color and texture make each pair one of a kind. Cream and brown accents let the special upper shine while bringing in The All-Americans classic detail, like ribbed toe bumpers, flat laces, and a throwback P.F. Flyers heel plate.
To style Wobbly Waffle for Winter, consider letting the standout craftsmanship take the lead. Paired with neutral pieces, the tactile texture draws attention. Use it to add a hint of this iconic pattern to your winter outfits or highlight the hand-dyed detail with matching colors and made-to-last pieces.
