28. MC Serch
Height of Style: "Product of the Environment" video
Signature Look: High-top fade and glasses
MC Serch did more than just prove that a white boy could do the running man while rocking a fade. His outerwear game was always on point. His glasses are a cool-guy-meets-nerdy style staple that still holds up today, and he took some risks—like rocking an ivory turtle neck while fishing in the middle of the ocean.