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The Best Dressed Oscar Winning Ladies of the Millennium

Updated September 23, 2021 4.8k votes 666 voters 9.5k views28 items

List RulesWomen 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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  • Photo: Wikimedia Commons / CC-BY

    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

     
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    Lupita Nyong'o won the 2014 Best Supporting Actress Oscar for her role as Patsey in 12 Years a Slave. Her beautiful blue Prada dress was on the top of a lot of "best dressed" lists that year. 

     
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  • Photo: Wikimedia Commons / CC-BY

    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

     
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    Cate Blanchett wore Armani Prive when she won the 2014 Academy Award for Best Actress for her role as Jeanette "Jasmine" Francis in Blue Jasmine. According to Vogue, this dress cost $100,000. 

     
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