The Best Crossover Shoes for Men

Five adventurous kicks that look good enough to wear in the office

Your weekday adventure shouldn’t be limited by the kicks on your feet. (Danner)
shoes

When you buy something using the retail links in our stories, we earn an affiliate commission that helps pay for our work. Read more about Outside’s affiliate policy.

Free time is tight, so you need to sneak in adventure when and where you can. That often means hitting a local trail at lunch or on the way home from work. It might not be Insta-glamorous, but these in-town micro-adventures keep you sane, so we found five pairs of shoes that can handle the rigors of trail use while still looking good in the office.

Danner Mountain 600 ($200)

shoes
(Courtesy Danner)

Most of Danner’s boots are so pretty you won’t want to get them dirty, but they really are built for the trail. The Mountain 600 combines Danner’s signature styling with an innovative Vibram midsole and outsole for super light, comfortable performance. And the gray blends in at the office.

Buy Now

Keen Winterhaven ($150)

shoes
(Courtesy Keen)

Keen took technology from their hiking line, like bamboo insulation and seam-sealed waterproofing, and layered it through this low profile leather boot that can handle any weather on the streets or the trail.

Buy Now

Timberland Killington ($110)

shoes
(Courtesy Timberland)

A hiking boot you could wear with a suit? Yep. Timberland somehow combines street-style sensibility with hiking performance features like mesh linings and OrthoLite footbeds for a full-grain leather boot that wouldn't look out of place in even the stuffiest office.

Buy Now

Forsake Phil Chukka ($130)

shoes
(Courtesy Foresake)

The classic Chukka styling looks good in the coffee shop or the cubicle, but the Phil also has a moisture-wicking liner, an open cell PU footbed, and a burly enough lug pattern on the outsole to provide traction on loose terrain. Plus it’s all wrapped up in a water-resistant leather package.

Buy Now

Fronteer Super Gratton Lo 2.0 ($140)

shoes
(Courtesy Fronteer)

These kicks were inspired by climbing shoes, but they’re built for everyday wear, with a comfy sneaker fit, molded sock liner, and water-resistant suede and canvas upper. But for those who like to stop by the gym after work, the super sticky sole and edging can handle light climbing, too.

Buy Now

Filed To: Hiking Shoes / Boots / Style / Casual / Gear
More Gear
More Gear