The Best Dressed Oscar Winning Ladies of the Millennium

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
    217 VOTES
    Sandra Bullock
    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

    Photo: Shutterstock
  • 2
    241 VOTES
    Lupita Nyong'o
    Photo: flickr / CC0

    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
  • 3
    195 VOTES
    Penelope Cruz
    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

    Photo: Shutterstock
  • 4
    203 VOTES
    Cate Blanchett
    Photo: flickr / CC0

    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. 

    Photo: Shutterstock
  • 5
    153 VOTES
    Octavia Spencer
    Photo: Metaweb / CC-BY

    Octavia Spencer won the 2012 Academy Award for Best Supporting Actress for her role as Minny Jackson in The Help. According to In Style, her Tadashi Shoji dress took 1,000 hours of work and a team of 10 to get it ready for the red carpet. 

    Photo: Shutterstock
  • 6
    229 VOTES

    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.