Leather Booties

Leather booties bring together timeless style and everyday versatility, making them a favorite for all kinds of adventures. Whether you’re heading out for a walk in the park or meeting friends in town, these boots offer a comfortable fit that’s easy to pair with just about anything in your closet. Crafted with care and designed to last, leather booties are ready to keep up with busy days and changing seasons—always delivering dependable comfort and classic appeal.

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Women's Stonington Boots, Moc Toe
Price was from: $170 now: $135.99

A rugged black moc toe boot with waterproof leather, sneaker-like comfort, and all-day support.

Pros: Great fit Versatile Comfortable Well made Looks great
Women's Stonington Chelsea Boots, Leather
Price was from: $150 now: $119.99

A rugged dark oakwood leather chelsea boot with sneaker-like comfort and durable rubber outsole.
Women's TOMS® Everly Chelsea Boots, Nubuck
Price was from: $119.95 now: $99.99

A stylish black nubuck leather ankle bootie with a 2 3/4" stacked heel and cushioned OrthoLite® insole.
Women's Blundstone 9500 High Top Chelsea Boots

A stylish and versatile leather boot with cushioned insole, shock absorption, and non-slip protection.
Adults' Blundstone 500 Chelsea Boots

A pair of premium black leather pull-on boots with shock-absorbing construction and cushioned comfort.
Women's Bean Boots, 8"

A Maine-made, weather-ready boot with a supple leather upper and durable rubber outsole, perfect for wet conditions.
Women's Eco Bay Chukka Boots, Leather

A consciously-crafted black nubuck leather chukka boot with recycled materials and a grippy rubber outsole.
Women's Frye Kate Harness Boots

A brown premium leather pull-on boot with iconic harness detail, cushioned insole, and durable rubber outsole.
Women's Bean Boots, 6.5" Chelsea

A beautifully crafted Chelsea boot with buttery-soft leather and waterproof rubber bottom for wet conditions.
Adults' Blundstone 550 Chelsea Boots

A pair of rustic black leather pull-on boots with superior shock absorption and cushioned comfort.
Adults' Blundstone 550 Chelsea Boots

An antique brown leather pull-on boot with superior shock absorption and cushioned comfort for all-day wear.
Women's Camden Hills Chelsea Boots
Price was from: $190 now: $94.99

A stylish Chelsea boot with full-grain leather, rubber outsole, and cushioned EVA footbed for all-day comfort.
Women's NextVenture Boots, Chelsea
Price was from: $150 now: $111.99

A tan Chelsea boot with waterproof nubuck uppers, cushioned EVA midsole, and Vibram rubber outsole for traction.
Women's Blundstone Heeled Chelsea Boots

A versatile slip-on boot with a 2" heel, featuring weatherproof leather and durable thermoplastic outsole.
Women's Bean Boots, 8" Shearling-Lined Insulated

A pair of tan and brown leather boots with plush shearling lining and waterproof rubber bottoms.

Pros: Waterproof Well-made Warmth Durable Comfortable
Men's Stonington Boots, Moc-Toe

A rugged dark oakwood leather boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.

Pros: Durable construction Versatile use Lightweight design Stylish appearance Comfortable fit
Women's Bean Boots, 10" Shearling-Lined

A Maine-made boot with shearling lining, Thinsulate™ insulation, and waterproof leather/rubber for cold, wet conditions.

Pros: Comfy Good customer service High-quality shearling Durable Warm
Men's Bean Boots, 6.5" Chelsea

A waterproof Chelsea boot with a soft leather upper and durable rubber bottom, perfect for wet conditions.
Men's Bucksport Boots, Cap Toe
Price was from: $200 now: $169.99

A rugged coffee bean-colored boot with waterproof oiled-leather upper, Vibram® rubber outsoles, and anti-odor liner.

Pros: Quality construction Waterproof High comfort Rugged color Durable outsoles
Women's Bean Boots, 8" Fleece-Lined Insulated

A cozy, fleece-lined boot with suede leather and waterproof rubber, perfect for wet and cold conditions.

Pros: Attractive look Good fit Comfortable to wear
Women's Bean Boots, 8" Flannel-Lined Insulated

A Maine-made boot in soft leather with flannel lining, perfect for wet, cold conditions.

Pros: High quality Perfect fit Soft leather Warmth Quick break-in
Women's Stonington Chelsea Boots, Suede
Price was from: $150 now: $119.99

A rugged, graphite suede Chelsea boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.
Women's TOMS® Everly Chelsea Boots, Suede
Price was from: $119.95 now: $99.99

An oatmeal suede leather ankle bootie with dual gore panels and a 2 3/4" stacked heel.
Women's Wicked Good Lodge Chukkas
Price was from: $140 now: $111.99

A cozy brown suede chukka bootie lined with genuine Australian lamb shearling and featuring a durable rubber outsole.

Leather Booties

When the days grow shorter and the air takes on a crisp edge, there’s nothing quite like reaching for a pair of leather booties to see you through the season. These dependable shoes have a way of fitting seamlessly into everyday life, whether you’re dashing out the door for a morning coffee run, heading into the office, or meeting friends for an evening stroll beneath twinkling holiday lights. Leather booties are beloved for their ability to blend comfort with timeless style, offering a sturdy foundation for all kinds of winter adventures. Their low-profile design makes them easy to slip on and off, while the durable leather construction stands up to busy days and unpredictable weather. You’ll find they’re just as at home paired with your favorite jeans and a cozy sweater as they are with a dress and tights for a festive gathering. It’s this versatility that makes leather booties a smart addition to any closet, and a thoughtful gift for anyone who appreciates practicality and style in equal measure.

Gifting a pair of leather booties can feel like sharing a little piece of everyday comfort—something that’s both useful and meaningful, especially in the colder months. They’re a great choice for anyone who’s always on the move, from teachers who spend their days on their feet to friends who love exploring new neighborhoods, or family members who enjoy weekend getaways. The durable soles offer steady footing on frosty sidewalks, while the supple leather molds to the shape of your foot, promising comfort that lasts all day long. Quality leather booties are built to handle whatever the season brings, making them a reliable companion for winter errands, holiday festivities, and spontaneous walks when the first snow begins to fall. And with so many styles to choose from—classic, rugged, or refined—it’s easy to find a pair that suits anyone’s personal style. If you’re looking to expand your options, you might also want to explore our selection of Black Booties, which offer a timeless look that pairs well with just about everything.

Choosing the right pair of leather booties comes down to a few key considerations. Think about how you’ll wear them: a sturdy sole and cushioned footbed are ideal for days spent on your feet, while a sleek silhouette can easily transition from work to weekend. Look for thoughtful details like easy-on zippers, weather-resistant finishes, and classic stitching that add both function and flair. Leather booties are designed to age gracefully, developing a unique patina over time that tells the story of every outing and adventure. They’re easy to care for, too—a quick wipe with a damp cloth and the occasional conditioning treatment will keep them looking their best season after season. Whether you’re shopping for yourself or searching for a gift that’s sure to be appreciated, leather booties offer lasting value, dependable comfort, and enduring style that stands up to winter and beyond.

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