Not so long ago, boots—real boots—were reserved for a handful of select occupations. Tough jobs like construction, logging and factory work that required sturdy shoes to stand up to the pounding their wearers would dole out on a daily basis. Those guys knew what they needed out of a pair of heavy duty leather boots, and the hard-wearing footwear they wore back then inspired the designs we see today. Boots built with integrity and strength, but crafted with lighter materials and handsomely tanned leathers. With their rugged backwoods origins, they give an outfit a dissident, but attractive flavor without channeling the urban lumberjack look of a few years back. And if your office has a relaxed dress code, pair them with some chinos and a cardigan for a pleasant juxtaposition. But whatever you do, don't baby them. These boots were meant to be scuffed up—embrace it like a scar. Our imperfections tell a better story than any shine.