Fashionable Boots

Fashionable boots bring together timeless style and everyday versatility, making them a favorite choice for all kinds of adventures. Whether you’re heading out for a brisk walk or meeting up with friends, these boots are designed to fit right in with your active lifestyle. Comfortable and durable, they offer lasting value you can count on season after season. Explore a range of fashionable boots that pair effortlessly with everything from jeans to dresses, so you can step out confidently wherever the day takes you.

Sort by:

Filter & Sort

476 Items

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

A rugged dark oakwood leather boot with sneaker-like comfort, waterproof protection, and a durable rubber outsole.

Pros: Great fit Versatile Comfortable Well made Looks great
Women's Stonington Chukkas, Suede
Price was from: $109 now: $53.99

A rugged, classic navy suede chukka boot with leather lining and VertiGrip rubber outsole for all-day comfort.

Pros: Comfortable design Good traction Bean quality Warmth Great appearance
Men's Bean Boots, 6.5" Chelsea
Price was from: $160 now: $134

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

A rugged coffee bean leather boot with Vibram® rubber outsoles and waterproof oiled-leather upper.

Pros: Quality construction Waterproof Great color High comfort Useful side pockets
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 Blundstone 9500 High Top Chelsea Boots

A versatile pair of rustic black leather Chelsea boots with cushioned insoles and non-slip polyurethane outsoles.
Adults' Blundstone 550 Chelsea Boots

A pair of rustic black leather pull-on boots with superior shock absorption and cushioned comfort.
Men's Portland Boots, Lace-Up

A heritage-inspired dark russet leather boot with a Vibram® rubber outsole for durability and traction.
Adults' Blundstone 550 Chelsea Boots

A pair of antique brown leather pull-on boots with supreme shock absorption and cushioned comfort.
Adults' Blundstone 500 Chelsea Boots

A pair of premium brown leather pull-on boots with shock-absorbing construction and cushioned comfort for all-day wear.
Men's Stonington Chelsea Boots, Suede
Price was from: $150 now: $124

A rugged, deepest brown suede pull-on boot with sneaker-like comfort and high-performance cushioning.
Women's Bean Boots, Rubber Mocs

A weather-ready slip-on boot with durable leather, waterproof rubber, and enhanced comfort for wet conditions.
Women's Camden Hills Alpine Boots

A rugged black alpine boot with full-grain leather, wool lining, and VertiGrip rubber outsole for versatile traction.
Men's Stonington Chelsea Boots, Leather

A rugged dark oakwood leather pull-on boot with sneaker-like comfort and durable VertiGrip rubber outsole.
Men's Stonington Boots, Suede Moc-Toe
Price was from: $170 now: $144

A rugged, deepest brown suede moc-toe boot with sneaker-like comfort and durable rubber outsole.
Women's Stonington Boots, Suede Moc-Toe
Price was from: $149 now: $119

A rugged, light gold suede moc-toe boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.
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 Frye Campus 14L Boots

A versatile black leather boot with premium construction and a classic round toe, handcrafted for lasting quality.
Women's Bean Boots, 8" Insulated

A weather-ready boot with supple leather, waterproof rubber, and cozy insulation for ultimate comfort and durability.
Women's Bean Boots, 6"

A weather-ready, Maine-made boot with supple leather, durable rubber, and enhanced comfort for wet conditions.
Men's Bean Boots, Rubber Mocs

A Maine-made, waterproof moc with a supple leather upper and durable rubber sole, perfect for wet conditions.
Women's Camden Hills Chelsea Boots
Price was from: $190 now: $94.99

A stylish Chelsea boot with full-grain leather, cushioned EVA footbed, and rugged rubber outsole for versatile traction.
Women's Bean Boots, 6.5" Chelsea

A beautifully crafted Chelsea boot with buttery-soft leather and waterproof rubber bottom for wet conditions.

Fashionable Boots

As the air turns crisp and the leaves begin to show their colors, there’s something special about pulling on a great pair of boots and heading outside—whether you’re strolling through town, meeting friends for coffee, or taking the scenic route on your daily walk. Boots have a way of grounding you, both literally and figuratively, offering comfort and confidence with every step. When it comes to choosing the right pair, it’s about finding the perfect balance: boots that look good and feel even better, that stand up to everyday adventures and keep pace with your plans, no matter the weather. You want boots that are built to last, with durable materials and thoughtful details that make them easy to wear all day long. And of course, it helps when they’re versatile enough to go from weekday errands to weekend outings without missing a beat.

When shopping for boots, consider where and how you’ll wear them most. For many, a reliable pair of boots becomes a go-to choice for everything from apple picking with the family to brisk walks through the park. They’re also a thoughtful gift for someone heading off to college, a friend who loves spending time outdoors, or anyone who appreciates a blend of comfort and style. Look for features like sturdy soles that offer good traction, supportive insoles that keep feet happy on longer days, and uppers that are easy to clean after a little mud or rain. The best boots don’t just look great—they’re practical too, with timeless designs that never go out of style. Whether you prefer classic neutrals or something with a little more personality, there’s a boot to suit every taste and occasion. And as the season shifts, it’s worth having a pair ready by the door, so you can make the most of every crisp morning and golden afternoon.

No matter your routine, boots have a way of making everyday moments feel a little more special. They’re the kind of footwear you reach for when you want to feel put-together, protected from the elements, and ready for whatever the day brings. From bustling city streets to quiet country lanes, the right pair can carry you comfortably through it all. If you’re looking for more inspiration or want to explore a wider range of options, take a look at our collection of Stylish Outdoor Boots—each designed with quality, comfort, and timeless style in mind, so you can step confidently into the season ahead.

It's time to upgrade your browser

Fashionable Boots