Streetwear isn't dead, but it sure has calmed down these days. And you know what? Maybe it's time to take it beyond the J.Crew chambray and Redwings. Maybe you should go all-in The Playboy Club style—slick hair, proper suit, hard drink. Don't ditch the Nikes, but take a few cues from one of the great eras of men's style and get yourself some proper fitting behavioral and sartorial calling cards. Click on to see five elements from the Playboy era that the modern gentleman should apply to his style routine.