Actresses The Best Dressed Oscar Winning Ladies of the Millennium  

Fashion Ranker
4.7k votes 569 voters 8.6k views 29 items

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! 
 
1 236 VOTES

Sandra Bullock is listed (or ranked) 1 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo: via Pinterest

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

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2 212 VOTES

Penelope Cruz is listed (or ranked) 2 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo: via Twitter

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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3 221 VOTES

Allison Janney is listed (or ranked) 3 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo:  U-Celebs /YouTube

When she took home the Best Supporting Actress Oscar for I, Tonya in 2018, Allison Janney sported a gorgeous red Reem Acra gown with a plunging neckline, nipped in waist, and long, flowing sleeves. 

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4 250 VOTES

Lupita Nyong'o is listed (or ranked) 4 on the list The Best Dressed Oscar Winning Ladies of the Millennium
Photo: via Wikimedia

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. 

 
Photo: Shutterstock

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