Best Worst Dressed

8 Shocking Moments of the Year

UPDATED 09/23/2002 at 01:00 AM EDT • Originally published 09/23/2002 at 01:00 AM EDT

1 Chelsea Clinton's Makeover
Ditching her ringlets, the Oxford student turned international ingenue with dramatic makeup, a sleek new do—and sleek new pals Gwynnie and Madonna—at Versace's Paris show in January. "I'm a bit dazzled by it all," she said.

2 Brad Pitt's Hermit Moment
"It's past the prickly part," said a grateful Jennifer Aniston of the beard her husband grew for a much-delayed film. In August (above) he accessorized with beads.

3 Reading Julia Roberts
America's sweetheart sent out a cryptic message in March thought to be aimed at Vera Steimberg and her rumored refusal to grant a quick divorce to estranged husband Danny Moder so Roberts could marry him.

4 Winona Ryder's T Plea
The Girl, Interrupted star graced June's W in the tongue-in-chic T-shirt that hit the streets after she was arrested for allegedly shoplifting nearly $4,800 worth of goods from L.A.'s Saks Fifth Avenue.

5 Gwyneth's Gothic Horror
Paltrow's Oscar-night concoction—Alexander McQueen's sheer tulle, Heidi's hairdo, Elvira's eyeliner and her own unflattering slouch—was "unforgivable," said designer Randolph Duke. Viewers agreed.

6 Tom Cruise Braces Himself
Behind the megawatt smile, "I couldn't close my mouth properly," said the Minority Report star, still toothsome to the vast majority of fans despite bite-correcting braces put on in January. (They come off this mouth.)

7 Matt Lauer: Hair Today
... gone tomorrow, as he proved by getting a buzz cut in June. "I am just trying to beat Mother Nature to the punch," said the balding a.m. host.

8 Lagerfeld Loses It
Looking more like the models, Chanel designer Karl Lagerfeld, 64, showed off his 92-lb. weight loss at his July show by wearing Chanel women's jeans. Why the diet? "I wanted to feel 20 again," he said.