Timberland

It’s hard to imagine another footwear brand like Timberland that has been mentioned in rap lyrics decade after decade. The reason is quite practical: waterproof, comfortable, and durable work boots made it easier to hustle on the streets of New York. Soon, subcultures surrounding street life adopted the style, and the icon was born.

Founder Nathan Swartz was a shoemaker, as were three generations before him in his family. His family moved to the United States from Ukraine on the brink of World War I.