According to Timberland, the company's sales more than tripled in the '90s—the same time the boots became a huge part of hip-hop and urban culture. The '90s were all about the classic six-inch boots. We saw Das EFX, Mobb Deep, DMX, and more rock them in their videos, at performances, and at events. Biggie even name-dropped the brand in a verse when he said he liked black Timbs and black hoodies in "Suicidal Thoughts."