Red Wing 

Often imitated, but never duplicated, Red Wing is probably one of those heritage brands that have made the biggest strides the past few years. And why wouldn't they? Undoubtedly, the de facto boot of the heritage set is the 6" Moc. They've also made appearances on runways like designer Patrik Ervell, who kitted out his male models in the low-cut Postman shoe. The fact that they've gone from functional to fashionable without changing a thing shows this Minnesota brand hasn't lost a step since it's inception in 1905. 

6" Olive Mohave 8881 Boot, $350 

Suede/Nubuck Cleaner Set, $11 

Antique Cigar Beckman Moc 9030, $440