Trail To Town Shoes

Trail to Town Shoes are your go-anywhere solution for those who embrace adventure without compromising on style. These versatile shoes seamlessly transition from rugged trails to bustling city streets, offering the perfect blend of comfort and durability. Whether you're trekking through nature's wonders or exploring urban landscapes, Trail to Town Shoes provide the support you need for every step of your journey. With a range of designs that cater to outdoor enthusiasts and city dwellers alike, these shoes are crafted to keep up with your active lifestyle while maintaining a timeless appeal.

Sort by:

Filter & Sort

476 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
Men's Stonington Oxford Shoes, Plain Toe

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

Pros: Good looking Rain resistance Comfort True to size Non-slip soles
Men's Bean's Comfort Fitness Walking Shoes, Waterproof

A weatherproof, cushioned walking shoe with breathable polyester mesh upper and durable VertiGrip rubber outsole.

Pros: Fit Quality Comfort Durability Arch support
Men's Swift River Sport Flip-Flops
Price was from: $59.95 now: $49.99

A brown leather flip-flop with a cushioned EVA footbed and all-terrain VertiGrip outsole for comfort.

Pros: Nice color options Cute print Durable Good fit Comfortable
Men's Kennebec Slip-On Shoes

A versatile dark earth leather slip-on with True Comfort footbed and VertiGrip outsole for all-day wear.

Pros: High quality Nice looking Attractive color Perfect fit Comfortable
Women's Vacationland Shoes, Slip-On
Price was from: $110 now: $89.99

A lightweight black slip-on sneaker with waterproof leather and breathable mesh for summer adventures.
Men's HOKA Challenger 8 Trail Shoes

A lightweight green trail shoe featuring a recycled mesh upper, cushioned EVA midsole, and grippy 4mm lugs.
Men's Downeast Slip-Ons, Wool
Price was from: $110 now: $79.99

A cozy cocoa slip-on with a wool blend upper, cushioned EVA footbed, and durable rubber outsole.
Men's Trail Model X Ventilated Hiking Shoes

A water-resistant suede hiking shoe with breathable mesh panels and enhanced traction for wet surfaces.
Women's 1985 Mountain Classic Sneakers

A tan suede and nylon sneaker with exceptional cushioning, water resistance, and rugged VertiGrip rubber traction.
Women's VEJA Dekkan Trail Shoes

A lightweight trail sneaker with a recycled polyester upper and cushioned EVA midsole for all-day comfort.
Women's Downeast Clogs, Wool
Price was from: $99.95 now: $74.99

A cozy toasted coconut clog with a wool blend upper, cushioned EVA footbed, and durable rubber outsole.
Men's HOKA Anacapa 2 Freedom Hiking Shoes

A tan slip-on hiking shoe featuring cushioned sugarcane EVA midsole and grippy Vibram Megagrip outsole.
Women's Camden Hills Penny Loafers, Leather

A comfortable black leather penny loafer with a cushioned insole and durable rubber outsole for versatile wear.
Women's Everywhere Explorer Boots
Price was from: $109 now: $79.99

A rugged yet stylish mauve taupe hiking boot with suede leather, rubber, and water-resistant polyester ripstop fabric.
Women's Camden Hills Boots, Lace-Up
Price was from: $190 now: $151.99

A stylish black lace-up boot with full-grain leather, EVA footbed, and VertiGrip rubber outsole for all-day comfort.
Women's Downeast Slip-Ons, Wool
Price was from: $110 now: $79.99

A cozy, durable slip-on with a wool blend upper, suede rand, and grippy rubber outsole.
Women's Vacationland Sneakers, Lace-Up
Price was from: $110 now: $89.99

A lightweight white sneaker with waterproof leather, quick-drying mesh, and siped rubber outsole for traction.
Women's Camden Hills Chelsea Boots
Price was from: $190 now: $151.99

A stylish oakwood Chelsea boot with full-grain leather, rubber outsole, and cushioned EVA footbed.
Men's Comfort Walkers 2, Ventilated

A lightweight gray walking shoe with a water-resistant suede upper and temperature-regulating lining.
Men's Elevation H2O Shoes

A lightweight gray water-friendly shoe with breathable nylon/neoprene, convertible heel, and grippy VertiGrip outsole.

Trail To Town Shoes

When the call of the trail is just as strong as the pull of your favorite downtown café, trail to town shoes are the answer for those who want to move seamlessly between outdoor adventures and everyday errands. These versatile shoes are purposefully designed to handle the varied demands of both rugged paths and city streets, offering the durability and grip you’d expect from outdoor gear, paired with the comfort and style that fit right in at a casual get-together or a stroll through the park. As winter deepens and the days alternate between crisp, snowy mornings and slushy, salt-lined sidewalks, the right footwear becomes even more essential. Trail to town shoes are built to take on unpredictable January weather, with outsoles engineered for traction on everything from muddy paths to icy pavement, and uppers that stand up to the elements while still looking sharp. If you’re searching for a pair that can keep pace with your on-the-go lifestyle—whether you’re walking the dog before work, catching up with friends after a hike, or navigating busy sidewalks—these shoes are a smart and practical choice.

Choosing the right pair of trail to town shoes comes down to a few key considerations. Comfort is paramount, especially if you’re planning to wear them all day, so look for features like cushioned midsoles, supportive footbeds, and lightweight construction that won’t weigh you down. Many casual trail shoes are crafted with flexible materials that move with your foot, providing the freedom you need for everything from spontaneous detours on a wooded path to quick errands around town. Durability is another hallmark of this footwear category—reinforced toe caps, sturdy outsoles, and thoughtfully designed uppers mean you can count on them to last season after season. For those who value lasting value and timeless style, these shoes offer a look that’s equally at home with hiking pants or jeans, making them an easy addition to any wardrobe. They’re also a thoughtful gift for anyone who loves to stay active outdoors or simply appreciates the ease of a shoe that does it all—ideal for travelers, students, busy parents, or anyone who prefers to pack light and stay ready for whatever the day brings.

Trail to town shoes are more than just practical—they’re about enjoying every moment outside, no matter where it takes you. Picture a weekend that starts with a brisk walk through frosty woods, continues with a stop at your favorite coffee shop, and ends with errands around town—all without ever needing to change your shoes. These are the kinds of days that inspired the design of trail to town shoes: days full of possibility, movement, and connection. They’re perfect for those who want to make the most of winter’s beauty, offering the kind of versatility and comfort that encourages you to stay out a little longer, explore a little farther, and enjoy the outdoors in every way. If you’re looking to expand your footwear options or find a reliable gift for someone who’s always up for a new adventure, you’ll find plenty of inspiration in our collection. For even more options built to handle trails and beyond, visit our dedicated Trail Footwear page to explore styles designed to keep you comfortable, supported, and ready for anything the season brings.

It's time to upgrade your browser

Trail To Town Shoes