Year It First Dropped: 2012

These days, it seems doing a collaboration with Mark McNairy is the new getting knighted. But we do have McNasty to thank for continuing to blur the line between the fashion and streetwear worlds. Before he dropped the Bee Line for Billionaire Boys Club collection with Pharrell, McNairy was already making moves with another well-known hip-hop icon: The Timberland boot. His 2012 collabo reimagined the 6-inch wheat boot with a pop of color at the heel and a luxe suede upper. While the equally classic "bread and broccoli" Field Boot got a dose of camouflage pattern, another of McNairy's signatures. Known for his quirky designs, the zippable Radler Trail Camper Flats done up in colors similar brick-soled bucks paid homage to the designer's rebel prep sensibilities.