5. Ari Gold
Show (Air Dates): Entourage (2004-present)
Actor: Jeremy Piven
Want to know how to rock a fuck-you suit to perfection? Look no further than Entourage's Ari Gold, who just reeks of swag, complete with a crazy expensive price tag. Whether in black, navy, shiny silver, or heather gray, Ari's sharply tailored two-piece sets, paired with clean pocket squares, crisp shirts, and smart ties, always make the guy next to him look like a schlub. And that's precisely the point.