Lil Wayne was dressing like Dipset with the whole rockstar look and the B.B. Simons belts. Weezy's whole style was heavily NY/Philly inspired he even filmed the Hustler Muzik video in NYC...
Chief Keef's style is typical urban mixed with 5th Avenue style. His style of dress strongly resembles what dudes in NY were rocking in '09. NY nikkas attire was Polo Rugby, True Religions/Robins/Tavernitis or Cargos, J's, AF1's, or Polo Boots/Uggs/Asolos/Timbs, fitted World Series cap, Polo sweatsuits, B.B. Simons and designer belts, designer sneakers most notably the Pradas at that time, Pelle Pelle jackets. Keef ain't rocking shyt that we haven't been rocking. When drill came out I was surprised to see them nikkas dressed like us.