Think of fashion like the stock market: It’s all a matter of risk versus reward. And this year it was Hollywood’s men–sticking with blue-chip performers such as the classic suits favored by Prince William and George Clooney (near left)–who were the big winners. Still, no one can blame the women for wanting in on the millennium’s hot opportunities: plunging backs and necklines, belly-baring hip-huggers, leopard prints, leather, fluttery ruffles, stiletto-heeled boots, and did we mention color? Fashion’s savviest, including Heather Locklear and Jennifer Aniston, got exciting returns from the trends. But with the latest looks moving in and out of favor faster than NASDAQ’s tech stocks, many leading ladies came out losers–looking silly (Portia de Rossi, top left) and confused (Jennifer Love Hewitt). Our best tip: Buy smart, sell tomorrow.