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

504 Items

Men's Everywhere Explorer Boots
Price was from: $109 now: $79.99

A rugged, stylish urban hiking boot with suede leather, rubber, and water-resistant polyester ripstop fabric.
Women's Everywhere Explorer Shoes
Price was from: $99 now: $74.99

An urban hiker with a suede leather/rubber build, offering comfort, water resistance, and reliable traction.
Men's Double L Sneakers, Lace Up
Price was from: $99 now: $69.99

A versatile cocoa sneaker with a leather upper, rubber outsole, and cushioned insole for all-day comfort.
Men's Storm Chaser 5 Slip-Ons

A durable 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

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
Women's Mountainside Boots, Ankle Zip
Price was from: $99 now: $34.99

A water- and stain-resistant nubuck leather boot with side zip, offering sneaker-like comfort and surefooted traction.
Men's Kennebec Slip-On Shoes

A versatile asphalt leather slip-on with True Comfort footbed and VertiGrip outsole for reliable traction.

Pros: High quality Nice looking Perfect fit Stylish Comfortable
Men's Eco Woods Lace-Up Shoes, Canvas
Price was from: $79 now: $24.99

A pair of cayenne canvas shoes with recycled materials, offering all-day comfort and excellent traction.

Pros: Great value Stylish look Durable construction Versatile use All-day comfort
Men's Elevation Hiking Shoes, Ventilated
Price was from: $130 now: $109

A lightweight gray mesh and rubber hiking shoe with ventilated, seamless comfort and grippy traction.

Pros: Comfortable for walking and hiking Attractive style Lightweight design Perfect fit for narrow feet Quality construction materials
Men's HOKA Challenger 8 Trail Shoes

A lightweight green trail shoe featuring a recycled mesh upper, cushioned EVA midsole, and grippy 4mm lugs.
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 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 Danner Trail 2650 Hiking Shoes

A lightweight, versatile trail shoe with a suede-and-textile upper, offering excellent traction and all-day comfort.
Men's Trail Model X Ventilated Hiking Shoes

A water-resistant suede hiking shoe with breathable mesh panels and enhanced traction for wet surfaces.
Men's Elevation H2O Shoes

A lightweight gray water-friendly shoe with nylon and neoprene, featuring quick-dry mesh and cushioned comfort.
Women's Camden Hills Boots, Lace-Up
Price was from: $190 now: $151.99

A stylish dark barley lace-up boot with full-grain leather upper and durable VertiGrip rubber outsole.
Women's Double L Sneakers, Lace Up
Price was from: $99 now: $74.99

A versatile toasted coconut sneaker with a leather upper, rubber outsole, and plush True Comfort insole.
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.
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 VEJA Dekkan Trail Shoes

A lightweight trail sneaker with a recycled polyester upper and cushioned EVA midsole for all-day comfort.
Men's Vacationland Sneakers, Lace-Up
Price was from: $110 now: $89.99

A lightweight blue sneaker with waterproof leather and breathable mesh, perfect for summer adventures.

Trail To Town Shoes

As the days grow longer and the promise of summer adventures beckons, the transition from rugged trails to urban landscapes becomes a frequent journey for many outdoor enthusiasts. Trail to town shoes embody the spirit of versatility, merging the robust features of outdoor footwear with the stylish aesthetics suitable for casual city outings. These shoes are designed for those who crave the freedom to explore without the need to switch gear. They are perfect for the weekend warrior who might find themselves hiking a scenic trail in the morning and meeting friends for a casual dinner downtown in the evening. The seamless transition these shoes provide caters not only to the practicality of carrying less but also to maintaining a sense of style that is appropriate for social settings.

When considering the purchase of trail to town shoes, it's essential to focus on certain key attributes that enhance both functionality and comfort. Durability is a cornerstone, as these shoes must withstand the varied demands of outdoor terrains while resisting wear and tear from urban environments. Comfort is equally crucial; the ideal pair features supportive insoles and responsive cushioning, ensuring that your feet are well cared for during long days. Look for soles with good grip that can handle both the unpredictability of nature’s paths and the slick surfaces of city streets. Moreover, the aesthetic design should not be overlooked. The best trail to town shoes offer a range of styles that fit naturally into your everyday wardrobe, making them a superb gift for those who appreciate practical yet stylish solutions.

For those who are more inclined towards rigorous hiking, pairing trail to town shoes with specialized Trail Hiking Boots can be a wise decision. This combination ensures that you're well-equipped for any outdoor adventure while still ready to step into a more urban setting without missing a beat. As spring unfolds into summer, these footwear choices become particularly relevant. The ability to move from an active morning to a relaxed evening without the need for a wardrobe change is not only convenient but also enhances the enjoyment of both natural and urban landscapes. Whether you're buying for yourself or choosing a thoughtful gift for a friend who loves to blend outdoor activities with city life, trail to town shoes are an excellent choice that supports a dynamic lifestyle with comfort and ease.

It's time to upgrade your browser

Trail To Town Shoes