2. Young Dro
Consistency goes for miles when it comes to menswear, and Young Dro has that in spades. Whereas many hardcore 'Lo heads opt for the brand's heyday of '90s Snow Beach anoraks and suicide ski jackets, Dro keeps it classy in prep-inspired gear that also accurately reflects the South's own propensity for looking dapper. Young Dro is perpetually in his Sunday best, even if he's wearing bright orange cargo shorts and a nautical-striped polo shirt.