Winter Slip On Shoes

Step into the season with ease and warmth with our collection of winter slip-on shoes, designed to keep you comfortable and stylish no matter where your adventures take you. These versatile shoes are crafted with quality materials that promise lasting value, making them an essential addition to your winter wardrobe. Whether you're heading out for a brisk walk or simply running errands around town, our slip-ons offer the perfect blend of durability and timeless style. Embrace the outdoors with confidence, knowing that each pair is built to withstand chilly temperatures while providing exceptional comfort and support.

Sort by:

Filter & Sort

298 Items

Men's Storm Chaser 5 Slip-Ons

A tough, all-weather slip-on with waterproof leather, rubber outsole, and exceptional cushioning for cold, wet conditions.

Pros: High quality Warm and cozy Versatile design Easy to slip on Comfortable fit
Women's Rugged Wellie® Shoes, Slip-On

A pair of black rubber slip-on shoes with a waterproof upper and durable VertiGrip outsole for wet conditions.

Pros: Easy to slip on/off Waterproof Durable Comfortable Good fit
Women's Downeast Slip-Ons, Wool

A cozy, thermoregulating wool slip-on with a suede rand and durable VertiGrip rubber outsole for reliable traction.
Women's Wicked Good Slippers, Squam Lake

A pair of brown suede leather slippers lined with genuine Australian lambswool for ultimate warmth and comfort.

Pros: Easy to slip on/off Good quality Warmth Comfortable Durable soles
Men's Comfort Mocs, Ventilated Slip-On
Price was from: $69 now: $54.99

A breathable, quick-drying slip-on with a knit mesh upper and pillow-like EVA footbed for ultimate comfort.

Pros: Lightweight Well-made Easy on/off Comfortable Good fit
Women's Back Cove Stretch Slip-Ons, Nubuck
Price was from: $74 now: $59.99

A lightweight, stretchy slip-on shoe with a soft loden nubuck upper and durable rubber outsole.

Pros: High quality Stylish design Attractive color options Good arch support Comfortable fit
Women's L.L.Bean Snow Boots, Suede
Price was from: $149 now: $129

A pair of ultra-warm, rosewood suede snow boots with waterproof shell and slip-resistant rubber tread.

Pros: Stylish look High quality Waterproof and dry Excellent warmth Comfortable fit
Men's Bean Boots, 8" Fleece-Lined Insulated Front Zip
Price was from: $199 now: $94.99

A cozy, fleece-lined boot with suede leather, rubber, and nylon, perfect for rain, snow, and cold conditions.

Pros: Easy to slip on and off Quality craftsmanship True to size fit Warmth Comfortable
Women's Eco Bay Leather Slip-Ons
Price was from: $89 now: $74.99

A pair of slip-on sneakers in slate or cool sea blue, featuring soft nubuck leather and recycled outsoles.

Pros: Cute look Stylish Versatile Good sole support Chic
Men's Kennebec Slip-On Shoes

A versatile slip-on with premium full-grain leather, True Comfort footbed, and VertiGrip outsole for reliable traction.

Pros: High quality Nice looking Perfect fit Attractive style Comfortable
Men's Mountainville Shoes, Penny Slip-On
Price was from: $109 now: $84.99

A casual woodsmoke leather loafer with an anti-odor footbed and excellent traction for all surfaces.
Women's Blundstone 500 Chelsea Boots

A lightweight, durable leather ankle boot with cushioned insoles and non-slip polyurethane outsoles.

Pros: Great fit Excellent durability Warm and cozy Lightweight design Comfortable to wear
Women's Forsake Lucie Waterproof Chelsea Boots
Price was from: $155 now: $129

A waterproof leather Chelsea boot with a breathable membrane, anti-odor lining, and excellent traction.

Pros: Attractive design Waterproof Warmth Versatile Comfortable
Men's Allagash Handsewn Mocs, One-Eye

A durable brown moccasin with full-grain leather and lightweight rubber outsole for superior comfort and traction.
Men's Downeast Slip-Ons, Wool

A cozy cocoa slip-on with a wool blend upper, suede rand, and durable VertiGrip rubber outsole.
Men's Bean Boots, Canvas Rubber Mocs
Price was from: $99 now: $84.99

A Maine-made, waterproof canvas moc with durable triple-needle stitching and a comfortable dual-density insole.
Women's Blundstone Heeled Chelsea Boots

A versatile black leather boot with a 2" heel, cushioned midsole, and durable thermoplastic outsole.
Adults' Blundstone 500 Chelsea Boots

A pair of premium leather pull-on boots with shock-absorbing construction and cushioned comfort in brown.
Women's Bean Boots, Slip-On Rubber Mocs

A waterproof slip-on moc with a tumbled leather upper and durable rubber outsole, perfect for wet conditions.
Men's Bean Boots, Rubber Mocs
Price was from: $99 now: $84.99

A Maine-made, waterproof slip-on boot with durable leather upper and long-lasting rubber outsole.
Adults' Blundstone 500 Chelsea Boots

A pair of premium leather pull-on boots with shock-absorbing construction and cushioned comfort for all-day wear.
Women's Eco Bay Boots, Leather
Price was from: $109 now: $49.99

A pair of eco-friendly slip-on boots with pebbled nubuck leather and a VertiGrip outsole for excellent traction.
Women's Storm Chaser 6 Slip-Ons, Waterproof

A waterproof slip-on shoe with a leather upper, fleece lining, and durable rubber outsole for wet conditions.
Women's Bean Boots, Rubber Mocs

A weather-ready slip-on boot with durable leather, waterproof rubber, and enhanced comfort for wet conditions.

Winter Slip On Shoes

As the brisk winds of winter begin to soften and the promise of spring stirs the air, it's an opportune time to reflect on the essentials that have seen us through the colder months. Among these, winter slip-on shoes stand out as a beacon of comfort, convenience, and warmth. Designed for ease and built to last, these shoes embody the spirit of winter living—where every moment outdoors is an invitation to embrace the season's unique beauty. Whether you're stepping out to gather firewood, heading to the local market, or simply enjoying a leisurely walk through a frost-laden park, slip-on shoes offer a seamless transition from indoor warmth to outdoor adventure.

The appeal of slip-on shoes during winter is universal, cutting across all ages and lifestyles. They serve not only as a practical asset for those who wish to avoid the fuss of laces but also as a thoughtful gift for loved ones who value comfort and style. Picture a grandparent delighting in the ease of slipping into a warm, sturdy pair of shoes on a chilly morning, or a busy parent appreciating the quick readiness as they juggle the demands of home, work, and play. These shoes are crafted to support every step with stability and provide a protective embrace against the cold, ensuring that every outdoor excursion is as enjoyable as it is essential. The durable materials and thoughtful design elements, like enhanced grip soles and insulating fabrics, reflect an understanding of winter’s demands, making these shoes a reliable companion through the season's unpredictable weather.

For those who find themselves often oscillating between casual outings and the need for a slightly more polished look, the versatility of slip-on shoes is unmatched. Transitioning effortlessly from a casual coffee date to an impromptu business meeting, these shoes are as adaptable as they are functional. If you're looking to expand your winter footwear collection with options that blend style with casual comfort, consider exploring our Winter Casual Shoes. Here, you'll find styles that maintain the same high standards of quality and comfort but are suited to a variety of settings and occasions. As winter gives way to the milder days of spring, these shoes remain a staple, proving their worth as a lasting investment in your comfort and style. Embrace the end of winter with footwear that stands the test of time and elements, ensuring that no matter the weather, your feet remain snug, supported, and stylish.

It's time to upgrade your browser

Winter Slip On Shoes