20. JENNIFER LOPEZ (2003)
This sari-style Valentino number in fresh mint green may have been the only good by-product of the age of Bennifer.
19. JODIE FOSTER (1995)
While she might be lambasted for it today, when Foster stepped out in this exquisitely beaded Armani in the mid-’90s, our collective fashion mind was blown.
18. CHARLIZE THERON (2000)
Years before she’d win her Oscar, Theron won over red-carpet watchers with her body-skimming tangerine Vera Wang.
17. KIM BASINGER (1998)
To pick up her Best Supporting Actress statuette for the ’50s-era flick L.A. Confidential, Basinger picked an appropriately retro-chic Escada.
16. KATE HUDSON (2003)
Sometimes it’s enough just to be pretty. Case in point: Hudson’s flawless turn in this golden gown by Versace topped with a carefully curled coif.
15. CLAIRE DANES (1997)
In a sea of spaghetti straps and taffeta, Danes brought a different silhouette to the Academy Awards when she arrived in an icy-cool sweater-skirt combo by Narciso Rodriguez that was as sleek as her new bob.
14. KATE WINSLET (2002)
Red always makes a statement, but Winslet made it one for the ages in this simple Ben de Lisi column set off with a single floral garland.
13. WINONA RYDER (1994)
Just a month after her Gen-X flick Reality Bites premiered, Ryder traded coffeehouse grunge for ultra-glam with a vintage flapper gown.
12. REESE WITHERSPOON (2007)
The newly single star capped off a winning awards-season red-carpet run with this subtly shaded and totally stunning Nina Ricci design.
11. GWYNETH PALTROW (1999)
For her fairy-tale moment — accepting the Oscar for her lead turn in Shakespeare in Love — it was only fitting that Paltrow wore a princess-worthy Ralph Lauren gown.
10. CATE BLANCHETT (1999)
The Elizabeth star’s John Galliano gown revealed its true beauty on the back side with an ornately embroidered Garden of Eden design.
9. ANNE HATHAWAY (2009)
From the twist of her chignon to the swirl of her Armani Privéskirt, Hathaway’s look was sterling perfection.
8. HALLE BERRY (2002)
The Monster’s Ball star made Oscar history with her 2002 Best Actress win — and fashion history for this Elie Saab gown with its strategically placed appliques.
7. ANGELINA JOLIE (2004)
White never looked less innocent than when Jolie picked a plunging Marc Bouwer halter to slink down the Academy carpet.
6. RENÉE ZELLWEGER (2001)
Before she garnered buzz for Bridget Jones’s Diary, the actress caught our eye in a lemon yellow vintage Jean Deesès dress.
5. SHARON STONE (1998)
While 1996 was the first time Stone brought high-low fashion to the Oscars with a Gap tee, this white button-down and Vera Wang skirt was the best.
4. MICHELLE WILLIAMS (2006)
Williams left her Dawson’s Creek days behind when she hit the carpet in a sophisticated mustard Vera Wang and bold red lips.
3. JULIA ROBERTS (2001)
The pretty woman made old things new again when she wore vintage Valentino — then an awards-show rarity — to scoop up her Best Actress Oscar for Erin Brockovich. She still owns the dress.
2. NICOLE KIDMAN (1997)
Stepping out in a striking chartreuse John Galliano for Dior number helped Kidman step out from then-husband Tom Cruise’s shadow. ”It represented John’s unique talent,” she said later. ”It was an honor to wear it.”
1. PENÉLOPE CRUZ (2007)
The color, the fit, and that train: With one swoop of her Atelier Versace gown, Cruz set the standard for Oscar fashion.