The No. 1907 boot, $230 at RedWing

Not So Fancy

Menswear has always been rooted in function, so it's not surprising that one of the most prevailing trends this fall is the pragmatic workwear of yesteryear. Stylish guys, more familiar with websites than job sites, are seeking out canvas coal bags or denim railroad jackets—often recreated by savvy brands in Sweden or Japan. But no piece personifies the trend like a pair of American-made Red Wing boots. The Minnesota-based company has outfitted hardworking guys for more than a century and recently introduced a new Lifestyle range, with vintage-inspired styles complimenting the boot's rugged proportions, oiled leathers and signature white outsoles. Just the act of lacing them up is an exercise in masculinity. Though originally worn with coveralls, Red Wings pair perfectly with a shirt and tie or flannel trousers. And don't worry about scuffs. They can handle it.

The original retail price of a new pair of Red Wing work boots in 1905.

Growing up in Iowa, my dad wore Red Wings for work because he was blue-collar. But he wore them after he had clocked out, too. I remember buying my first pair when I was just nineteen. Back then, I was one of the few who broke the rules—wearing work shoes just because. Now, those boots have completely  crossed all boundaries and are no longer limited to working. It just shows how much fashion has changed, and really makes you wonder what's next, doesn't it?

- Tim Hamilton, designer

Iron Ranger, $275, Gentleman Traveler, $245 and Classic Lifestyle, $235.

  • Soldiers in the first World War were issued Red Wing No. 16 boots.

Jason Schwartzman, Kanye West, Justin Timberlake, Wyclef Jean, Milo Ventimiglia and Michael Bastian.