Justin Timberlake, 2000
Even the most stylish celebrities had a time when they weren't so fashion savvy. Back in the day even we fell for this boy band heartthrob, afro and all. Lucky for us (and him), he's cropped his hair and transformed into a trendsetting tastemaker.
Jennifer Lopez, 1997
Simon Cowell would have voted this "American Idol" stunner off the stage for sporting this mile-high hairdo, and at the Oscars no less.
Taylor Swift, 2006
What a difference a few years and a ton of awards can make! Swift has climbed the charts and the best dressed lists since she released her first single in 2006. We're pretty sure country's golden girl will never rock THIS look again.
Scarlett Johansson, 2003
Though she's now considered one of the sexiest woman in the world, Scar Jo clearly had some help along the way. When she stepped out in this backless ensemble for the 2003 IFP Independent Spirit Awards, something about her outfit and mullet 'do was clearly lost in translation.
Melanie Griffith, 1987
Melanie Griffith arrived at the Golden Globes looking more like the winning statue than a celebrated actress. Despite her questionable ensemble, she went on to win a Golden Globe the following year for her unforgettable role in "Working Girl," a character that inspired women everywhere to accessorize their business suits with white sneakers.
Madonna, 1987
The Material Girl's style has always been cutting-edge, but even Brooke Shields would agree that her eyebrows need a little grooming.
Sarah Jessica Parker, 1980
No, this isn't a Gap ad, it's a young SJP. Although she clearly had style as a child star, it's amazing to think that this young lady would become THE fashion icon of the new millenium.
Heather Locklear, 1987
We know that "Dynasty" had some wild costumes, but this outfit wasn't even cool in the 1980's. Just seven years later our favorite neighbor from "Melrose Place" found herself on the cover of "Rolling Stone" and "People" magazine's list of the "50 Most Beautiful People."
Reese Witherspoon, 1999
Whoever allowed Witherspoon to wear this frumpy handmade shirt had cruel intentions. Luckily, Americas' Sweetheart has gracefully evolved into a red-carpet stunner.
Tori Spelling, 1997
Spellings getup(打扮) for the premiere of "The House of Yes" came from the fashion house of "no". Luckily, the mother of two has adopted a much cuter style. Hey, it WAS the 90's!