Winter Athleisure Shoes

Winter athleisure shoes are designed to keep up with active days and changing conditions, offering comfort and style that transitions easily from outdoor adventures to everyday errands. With a focus on durability and lasting value, these versatile shoes are made for those who want reliable performance and timeless appeal throughout the colder months. Whether you’re heading out for a walk or meeting up with friends, you’ll find options that deliver the quality and ease L.L.Bean is known for—all while keeping your feet feeling great all season long.

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Men's Snow Sneaker 5 Insulated Boots, Zip-Front

A zip-up winter boot with suede leather, rubber, and 200g ColdShield insulation for exceptional warmth and comfort.
Men's On Cloud 6 Shoes

A lightweight blue sneaker with a recycled mesh upper and cushioned Zero-Gravity foam midsole for comfort.
Men's HOKA Transport Shoes

A sustainable blue athleisure shoe with recycled materials and water-resistant features for active comfort.
Men's Snow Sneaker 5 Shoes, Slip-On

A slip-on winter sneaker with ColdShield insulation, stain-resistant suede, and a rugged VertiGrip rubber outsole.

Pros: High quality Comfortable design Roomy fit Durable construction Excellent warmth
Men's Snow Sneaker 5 Shoes, Lace-Up

A versatile winter sneaker with suede leather, rubber, and 200g ColdShield insulation for warmth and comfort.

Pros: Great fit Good traction Comfortable Keeps feet dry Excellent warmth
Women's HOKA Transport Shoes

A sustainable purple athleisure shoe with recycled materials and water-resistant treatment for active comfort.

Pros: Attractive color Stylish design Comfortable fit
Men's Stonington Shoes, Moc-Toes

A rugged, dark cocoa leather shoe with sneaker-like comfort, water-resistant protection, and durable rubber outsole.

Pros: Fit Quality Comfort Water resistance Versatility
Men's Urban Storm Shoes, Waterproof Insulated

A waterproof, insulated oakwood shoe with leather upper and rubber outsole, offering all-day comfort and support.
Men's HOKA Challenger ATR 7 GORE-TEX Running Shoes

A high-cushion, waterproof running shoe with EVA foam midsole and Durabrasion rubber outsole for all-terrain traction.
Women's Boundless Shoes
Price was from: $119 now: $89.99

A sage-colored athleisure shoe with a breathable recycled polyester upper and durable rubber outsole.

Winter Athleisure Shoes

When the air turns brisk and daylight fades early, there’s something comforting about slipping into winter athleisure shoes that are built for both warmth and all-day comfort. Whether heading to the gym, running errands in town, or meeting up with friends for a walk in the park, the right pair of shoes can make all the difference. Winter athleisure shoes are designed to handle the unique challenges of the colder months—think chilly sidewalks, damp trails, and the need for versatile style that fits right in, whether you’re out and about or taking it easy at home. They blend the best of athletic performance and relaxed style, so you can move comfortably from one activity to the next without missing a beat. Many people find these shoes especially helpful when winter weather makes traditional athletic shoes feel too lightweight, but heavy boots seem like overkill. The right pair can be a thoughtful gift for anyone who enjoys staying active despite the cold—students walking across campus, busy parents on the go, or anyone who prefers a little extra warmth and cushioning during the winter months.

Choosing winter athleisure shoes often comes down to a few key considerations. Look for materials that offer both durability and comfort, with features like plush linings, supportive insoles, and uppers that help keep out the chill. A good grip is essential for navigating slippery sidewalks or frosty driveways, and easy on-and-off designs are always a plus when you’re juggling bags or heading out the door in a hurry. These shoes are made to be versatile—ready for a quick workout, a coffee run, or a day spent exploring local trails. Their timeless style makes them a reliable staple in any winter wardrobe, pairing well with everything from leggings and joggers to jeans and casual wear. For those who appreciate lasting value, winter athleisure shoes are a smart investment, offering season after season of reliable comfort and performance. If you’re looking for even more options focused on all-day warmth and easygoing comfort, be sure to browse our full collection of Winter Comfort Shoes for more inspiration.