Reese Witherspoon is considered one of the most fashionable young actresses in Hollywood.

She’s been seamlessly stylish on all her awards carpets for several years. And she earned rave reviews for her flawless 2006 awards season wardrobe, all designed by Nina Ricci’s (no relation to Christina) head designer Olivier Theyskens. His elegant purple ombre strapless chiffon Oscar gown is shown here.

But trust me, Reese wasn’t always so effortlessly pulled together. I stumbled upon one past fashion faux pas that’s well worth revisiting.


Believe it or not, this is Reese’s ensemble worn to the 1997 Vanity Fair Oscar party, just nine years ago.  Clearly, she didn’t yet have a stylist on staff to "flash test" her black top to make sure photographer’s lights wouldn’t reveal too much skin.

Over-exposure aside, this entire outfit is just wrong on so many levels. And how about that goofy red-lipped grin. See, don’t you feel better about your own fashion flaws after seeing Little Miss Perfect’s past style blunder?

Photo Credits/WireImage