Angelina Jolie
Well, not too much has changed. Angie still favors the goth look, but she’s managed to transition from creepy scary Morticia at the 2000 Oscars to Queen of the Beautiful People Morticia at the 2009 awards show.
Jessica Alba
We didn’t know it was possible to fit cargo pockets, random zippers and bell bottoms all on the same pair of jeans, but Jess proved us wrong at the 2003 Teen Choice Awards. Fortunately, she has since traded in her tomboy look for girlie dresses like the lilac Christian Dior number she wore to the 2009 Independent Spirit Awards.
January Jones
Back in 2000, when the Mad Men star was dating Ashton Kutcher, she would wear clunky shoes, a dowdy dress and a puffy coat to the red carpet. One critically acclaimed television show later, and it’s all “Here, January, wear this stunning Versace gown to the 2009 Emmys.” And so she wore it. Fiercely.
Halle Berry
From the 1998 Oscars to 2009’s Keep a Child Alive’s Sixth Annual Black Ball, the actress has always been about the sex on the red carpet. Halle’s kept it evolving from a lingerie slip-like number to a sophisticated sexy Kaufman Franco sequin dress, and we salute her for it.
Kate Winslet
Titanic was the star's second Oscar nomination, and she showed up to the 1998 ceremony looking so excited despite her homely green gown. Eleven years (and four noms) later, she finally won the top prize at the 2009 Oscars looking significantly more poised in a gray YSL Atelier one-shoulder gown.
Nicole Richie
Oh, remember The Simple Life when Nicole played the sassy vulgar friend to Paris Hilton’s perpetual dumb blonde? Just look how low-rent Nic looked back in 2003. Five years later, she was able to transform herself into a whole new person. There's no way Simple Nicole would ever have shown up to the 2008 Carousel of Hope Ball's red carpet actually looking classy in Reem Acra.
Katherine Heigl
This 2005 photo shows the Grey's star at the beginning of her TV career. But like any ambitious young actress, she yearned to make the movie-star thing happen and went all va-va-voom glamourous in a stunning Escada dress at the 2008 Oscars. She certainly looks the part, but the jury's still out on her movie star success.
Kim Kardashian
Our very own E! reality star is a shining example of what a difference a stylist can make. In just two years, Kim K. has gone from janky (pictured in 2007) to trendsetting sexy (in 2009).
Carrie Underwood
Once upon a time, the season-four American Idol winner, (pictured on the left in 2005), was just another girl from Oklahoma who apparently liked crimped hair. But then the professionals took over and helped the country singer become a princess in this Randi Rham gown at the 2009 Academy of Country Music Awards.
Drew Barrymore
Drew's always been a little bit of a weirdo (or "free spirit") on the red carpet. Back during the 1998 Oscars she wore daisies in her hair, but 11 years later at the 2009 Emmys, she went for a softer, more mature look in a gorgeous Monique Lhuillier gown. Yet somehow, she manages to keep her youthful and carefree glow.
Katie Holmes
It seems like just yesterday Katie was one of those moody Dawson’s Creek kids at the 1998 Emmys. Ten years later, she’s reached movie star status (one of the perks of being married to Tom Cruise) and has been granted access to pretty designer dresses like the Lavin number she wore to the 2008 Critics' Choice Awards. Worth it?
Anne Hathaway
Famed stylist Rachel Zoe stepped in to save the actress from her frumpy stylings. We offer as proof Anne's transformation from the 2005 Tony Awards into a serious fashionista dressed in a gorgeous Oscar De La Renta at the 2009 Tonys. It’s like The Princess Diaries but real life.