Is it preferable to blaze forth into the newest craze, or to switch into reverse and embrace timeless classics? The answer depends on who you are. Even in the limited celebrity universe, different rules apply to hip-hop star Sean “Puffy” Combs (page 98) than to, say, Marie-Chantal of Greece (page 100). But rappers or royalty, those in it for the long haul “are not afraid to wear fashion,” says designer Marc Bouwer, one of eight notable judges (page 91) whose brains we picked to determine the style winners and losers of the year. The worst dressers exhibit the corollary to Bouwer’s theory: They let fashion wear them. If you can’t tell the difference between the true showstoppers and the mere show-offs, we’re here to help. In the next 75 pages, you’ll learn Billy Bob’s boo-boos and get a course in (Minnie) Driver’s ed.