Charles Oakley represents the old school. Although the six-foot-nine power forward was a clotheshorse, he was also one of the hardest-nosed players ever to wear warm-ups—and he still takes suiting up seriously. "When we get a contract, that's our job," he says. "You got to come to work and be a professional—and look like a professional." In other words: You wear a suit.
The outspoken 45-year-old former All-Star was one of the few players who voiced support for the NBA's dress-code, which was instituted in 2005, and when we sat down with him to discuss the state of NBA style, he couldn't hide his displeasure at professional basketball players' slovenly ways. "Why would I want to look like someone laying on the sidewalk can't get no food, can't get this, can't get that, can't get a suit and wear it on a consistent basis?! It's embarrassing." As with any career, however, Oakley knows that dressing for the job is not enough to help you excel. "I'm not going to sell all that," he says, breaking into a smile. "I hope no one's going to buy $20,000 worth of clothes and think that means they'll get 20 points that night. Just shoot."
Check out the photo gallery to see which players, coaches, owners, and announcers meet Oakley's sartorial standards—and who fouls out.