Men Boots

The Weekender Chukka combines casual style with all-day comfort. The boot is supremely comfortable straight out of the box thanks to lightweight, flexible stitchdown construction. Worn with or without socks, the Weekender Chukka channels a relaxed vibe so comfortable you...

The Red Wing Shoes 3321 Weekender Chukka Hawthorne Muleskinner is a Red Wing style from The Weekender Collection and inspired by our classic Chukka silhouettes. The Weekender Collection features Red Wing's traditional quality and craftsmanship in more flexible and lightweight designs...

The Classic Chelsea provides handcrafted comfort in a sleek, pull-on silhouette that features premium leather paired with the iconic Traction Tred outsole. The Red Wing 3192 Classic Chelsea in Hawthorne Muleskinner leather is a Classic Red Wing Chelsea Boot and is made in Red...

Stick to the dress code, free your feet. The Gobi III is a smart-casual men's desert boot that maximizes barefoot sensation and nurtures natural strength. GOBI OUTSOLEThe lifestyle sole offers maximum underfoot sensory feedback.CORK & RECYCLED PU INSOLEThe Everyday Cork...

The Postman Oxford was first built by Red Wing in 1954. The shoe was standard issue, government-approved footwear for mail carriers and police officers for decades. Look no further than Norman Rockwell’s iconic “The Postman” painting to see how ubiquitous...

This ankle boot, inspired by climbing shoes, was conceived with strips of rubber on both the shoe's front and back to provide better grip on steep and slippery terrain. Plain toe Boot, 4 Eyelets and 3 ski hooks.Leather lined model,...