These Trail-to-Town Boots Will Take You (Almost) Anywhere

From parks to peaks to backyard barbecues, these shoes are ready


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Choosing hiking boots, first and foremost, should be about comfort—but what about practicality? If you’re a do-it-all-in-a-day adventurer, you might be looking for a unicorn of a boot that’s equally at home on concrete and dirt. Luckily, boots like these have entered the gear market. While there are still plenty of options for utilitarian hiking gear, recent trends in outdoor apparel are melding technical capabilities with street appeal. We call this the trail-to-town trend, and it’s sweeping across many product categories.

“Brands are responding to an evolving consumer and their approach to outdoor recreation,” says Tad Summersett, a category merchandising manager at REI who specializes in footwear. “Many categories are seeing development of product that delivers versatility.”

This means you can have your cake and eat it too: Trail-to-town boots offer stability on the trail, durability for the long haul, and style for the before-and-after pit stops.

This trend has been developing for a while now, says Summersett, but this spring is a tipping point. Brands like Lowa and Keen have designed technical hiking shoes that are streamlined enough for town (or the office, if you’re lucky enough to work in a casual environment). Even if you don’t want to look like you’re headed to the trail on a daily basis, boots like these transition easily from a day hike to nearly any other plans your weekend holds.

Here are some of our favorite trail-to-town boots and how to style them.

Vintage-Modern Trail-to-Town Hiking Boots

If you’re a fan of the vintage-inspired outdoor gear movement that’s giving everything from fleeces to canvas bags a makeover to the tune of 1970-something, consider investing in some vintage-inspired trail-to-town hiking boots. Today, many boots feature heritage styling but come equipped with all of the modern features you’d expect from quality hikers, like weatherproof uppers and grippy outsoles. Technical trail-to-town boots with a vintage touch like the Timberland Mt. Maddsen, or old-school mountaineering, retro-style kicks like the Merrell Ontario are some of the best options you’ll find.

If you plan on hiking more technical trails, look for boots packed with features like waterproof leather uppers, rock plates and sticky outsoles. Rock these if your weekend schedule contains brewery tours, outdoor brunches, and spontaneous wet-weather hikes.

The Merrell Ontario boots feature Vibram soles for good grip.

Consider pairing the boots with slim-fitting cargo hiking pants and your favorite fleece or flannel for a mountain-ready outfit. Throw on clean jeans and a sweater when you get back to the car. These boots are often available in neutrals, so don’t be afraid to roll up your pants and flash some fun socks.

Women’s boots we love: Merrell Ontario, Timberland Mt. Maddsen

Men’s boots we love: Merrell Ontario, Timberland Mt. Maddsen

Pair them with:

Fitness-Forward Trail-to-Town Hiking Boots

If you’re more comfortable hiking in leggings than cargo pants, consider investing in a pair of trail-to-town boots designed to fit and feel like trail runners. These boots, like the Keen Terradora or the Salomon Outline, are perfect for both light hikes and fast summits. Lace ’em up if your weekend plans include sunrise mountain-peak yoga followed by an afternoon at the farmer’s market.

Pair the Keen Terradora boots with your favorite colorful socks.

Style with hiker tights for more demanding treks, and layer up top with a lightweight sweater or a vest. For a fitness-forward, warm-weather approach, let some ankle show with 7/8 leggings or tech shorts. When it’s time to turn to city streets, change into cuffed jeans or just carry on in your trendy athleisure.

Women’s boots we love: Salomon Outline, Keen Terradora

Men’s boots we love: Salomon Outline, Keen Venture

Pair them with:

Like Your Favorite Pair of Sneakers, but Rugged

If above-the-ankle boots aren’t your thing, there are plenty of low-cut options that pack a technical punch. These hiking shoes, like the Danner Jag Low, are somewhere between old-school tennis sneakers and approach shoes, and they often suit people who value freedom of movement over ankle protection. These sneaker-inspired boots are perfect for afternoon hikes that turn into early-evening barbecues.

Sport the Danner Jag Low shoes with your favorite leggings.

Wear these literally any way you would other tennis shoes: with jeans, ankle pants, a hiking skirt (yes, these are real and awesome) or joggers. If versatility with a bit of technical flare is your style, these are for you.

Women’s boots we love: Danner Jag Low, Keen Terradora Low

Men’s boots we love: Danner Jag LowMerrell Ontario Low

Pair them with:

No matter what your lifestyle or street aesthetic, hiking gear that transitions seamlessly from the city to the trail  is good news for all outdoor enthusiasts. Whether you want to rock high-tops, low-tops or tech-inspired running shoes, your feet will always be prepared for an adventurewhenever it comes time to hit the trail (dirt or otherwise).

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