Leather Heeled Boots

Step out with confidence and timeless style in leather heeled boots, the perfect blend of classic appeal and everyday comfort. Whether you're heading to the office, exploring your favorite shops, or meeting up with friends, these versatile boots are designed to pair effortlessly with a variety of outfits. Durable construction and quality materials ensure they’ll be a staple in your wardrobe season after season, making it easy to enjoy lasting value and dependable performance wherever your day takes you.

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298 Items

Women's Blundstone Heeled Chelsea Boots

A versatile black leather boot with a 2" heel, cushioned midsole, and durable thermoplastic outsole.
Women's Blundstone Blocked Heeled Chelsea Boots

A sleek, heeled Chelsea boot with water-resistant leather and Ortholite footbed for maximum comfort.
Adults' Blundstone 550 Chelsea Boots

A pair of rustic black leather pull-on boots with superior shock absorption and cushioned comfort.
Women's Frye Kate Harness Boots

A premium brown leather pull-on boot with iconic harness detail, cushioned insole, and durable rubber outsole.
Women's Blundstone 9500 High Top Chelsea Boots

A versatile, rustic black leather Chelsea boot with brogue detailing and outstanding shock absorption.

Pros: Durable Stylish True to size Versatile Comfortable
Women's TOMS® Evelyn Zip Boots
Price was from: $129.95 now: $109

A stylish tan low calf boot with premium leather upper and 2 3/4" stacked block heel.
Women's Frye Campus 14L Boots

A versatile black leather boot with premium construction and a classic round toe, handcrafted for lasting quality.
Men's Stonington Chelsea Boots, Leather

A rugged dark oakwood leather pull-on boot with sneaker-like comfort and durable VertiGrip rubber outsole.
Adults' Blundstone 550 Chelsea Boots

A pair of antique brown leather pull-on boots with supreme shock absorption and cushioned comfort.
Women's Stonington Chelsea Boots, Leather

A rugged dark oakwood leather chelsea boot with sneaker-like comfort and durable rubber outsole.
Women's Camden Hills Chelsea Boots

A stylish and durable oakwood Chelsea boot with full-grain leather upper and rugged rubber outsole.
Women's Bean Boots, 6.5" Chelsea

A beautifully crafted Chelsea boot in buttery-soft leather with a waterproof rubber bottom for wet conditions.
Women's Bean Boots, 8" Shearling-Lined Insulated

A Maine-made boot with buttery-soft leather, plush shearling lining, and waterproof rubber bottom for cold conditions.

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
Men's Bean Boots, 6.5" Chelsea

A black leather and rubber Chelsea boot with waterproof bottom, easy pull-on design, and reliable traction.
Women's Camden Hills Boots, Lace-Up

A stylish black lace-up boot with full-grain leather, cushioned EVA footbed, and VertiGrip rubber outsole.
Women's Maine Warden's Field Boot

A rugged, deepest brown leather boot with GORE-TEX, Primaloft insulation, and Vibram outsole for superior traction.
Men's Allagash Handsewn Chukka Boots

A pair of ash suede leather chukka boots with handsewn construction and a chunky lugged outsole.
Women's Bean Boots, 10" Shearling-Lined Insulated Side Zip
Price was from: $349 now: $309

A Maine-made boot with plush shearling lining, waterproof rubber bottom, and convenient side zipper.
Women's Camden Hills Alpine Boots

An icicle white alpine boot with full-grain leather, wool lining, and rugged VertiGrip rubber outsole.
Women's Storm Chaser 6 Lace-Up Boots, Waterproof Insulated

A waterproof, insulated boot with a faux fur collar, offering warmth and comfort in wet, cold conditions.

Leather Heeled Boots

When the air turns crisp and the leaves begin to rustle underfoot, leather heeled boots step into their own as a timeless choice for anyone who appreciates comfort, durability, and classic style. These boots have a way of elevating everyday moments, whether you’re heading out for a morning coffee, strolling through the farmers’ market, or meeting friends for a weekend lunch. The rich texture and substantial feel of leather bring a sense of confidence to every stride, while the added height of a heel offers just the right amount of lift—perfect for moving from workdays to evenings out without missing a beat. For those who spend plenty of time on their feet, the right pair of leather heeled boots can make all the difference, offering cushioned support and a secure fit that’s comfortable from the first step to the last. As fall settles in, these boots become a go-to layer, pairing effortlessly with your favorite jeans, cozy sweaters, or even a casual dress and tights, making them a versatile staple for the changing season.

Choosing the right leather heeled boots is all about balancing personal style with practical features that stand up to daily wear. Quality craftsmanship is key; look for sturdy soles, reliable stitching, and supple leather that only grows softer and more distinctive with age. Many folks appreciate boots with easy-entry features like side zippers or pull tabs, making it simple to slip them on and head out the door. For those who spend time outdoors—whether it’s cheering at a soccer game, exploring a pumpkin patch, or just enjoying a walk in the park—boots with a stable heel and solid tread offer dependable traction and comfort on a variety of surfaces. These boots also make a thoughtful gift for anyone who values lasting value and timeless style, from students heading off to college to loved ones celebrating a birthday or milestone. There’s something special about unwrapping a pair of leather heeled boots and imagining all the adventures ahead, from crisp autumn afternoons to snowy sidewalks and beyond.

Leather heeled boots are more than just a seasonal favorite—they’re a year-round essential that adapts to your needs and activities. They transition seamlessly from fall into winter, keeping feet warm and protected as temperatures drop, and their classic look never goes out of style. For those who are new to leather footwear, it’s worth taking a moment to read up on care tips, as a little attention goes a long way in maintaining the beauty and longevity of your boots. If you’re interested in exploring more options, or want to see the full range of styles and features available, take a look at our Leather Boots page for even more inspiration. Whether you’re searching for your next favorite pair or picking out a thoughtful gift, leather heeled boots promise quality, comfort, and a touch of everyday adventure with every step.

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Leather Heeled Boots