culture The Best Dressed Oscar Winning Ladies of the Millennium  

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List Rules Women who won an Oscar for Best Actress or Best Supporting Actress since 2000

The best dressed Oscar winning ladies of the Millennium know a lot about winning. Their gold statues and (more importantly) their gorgeous dresses prove just that! 

Celebrities' fashion choices are already big business, but Oscar fashion takes our obsession with what stars wear to a whole new level. The Academy Awards red carpet is an unparalleled runway for some of the best (and worst) celebrity fashion. Maybe it's the lights, or the golden glow of Oscar himself... but no where else do our favorite actresses shine brighter. 

When it comes to best dressed Oscar winners, Sandra Bullock, Helen Mirren, and Penelope Cruz always look stunning. And it makes sense that Oscar winners like Lupita Nyong'o (can we say blue Prada?) and Charlize Theron (gold Gucci to match Oscar) always make the lists of best dressed actresses at the Oscars. Check out this list of best dressed Oscar winning ladies of the millennium. Upvote the dress that wins them all! 
 
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Sandra Bullock


Sandra Bullock is listed (or ranked) 1 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo:  uploaded by The Wrap
Sandra Bullock wore this sparkly Marchesa dress when she won the 2010 Academy Award for her role as Leigh Anne Tuohy in The Blind Side

 
Photo: Shutterstock

Also Ranked

#9 on The Best American Actresses Working Today

#30 on The Best Actresses in Film History

#65 on The Greatest Actors & Actresses in Entertainment History

#8 on The Most Trustworthy Celebrities in the World

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Charlize Theron


Charlize Theron is listed (or ranked) 2 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo:  uploaded by The Wrap
When Charlize Theron won Best Actress for her role as Aileen Wuornos in Monster, she wore this gold Gucci dress.

 
Photo: Shutterstock

Also Ranked

#30 on The Best American Actresses Working Today

#54 on The Best Actresses in Film History

#98 on The Greatest Actors & Actresses in Entertainment History

#77 on The Most Trustworthy Celebrities in the World

see more on Charlize Theron
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Penelope Cruz


Penelope Cruz is listed (or ranked) 3 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo:  uploaded by The Wrap
Penelope Cruz wore this vintage Pierre Balmain dress when she won the 2009 Academy Award for Best Supporting Actress for her role as María Elena in Vicky Christina Barcelona

 
Photo: Shutterstock
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Cate Blanchett


Cate Blanchett is listed (or ranked) 4 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo:  uploaded by The Wrap
Cate Blanchett wore this lemon Valentino dress when she won the 2005 Academy Award for Best Supporting Actress for playing Katharine Hepburn in The Aviator

 
Photo: Shutterstock