Skip to main content

Great Outfits in Fashion History: Oprah in Vera Wang at the 2005 Legends Ball

She's worn a lot of Vera Wang over the years, but this remains a favorite.
Oprah Winfrey attends the Legends Ball 2005

There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In 'Great Outfits in Fashion History,' Fashionista editors are revisiting their all-time favorite lewks.

If you look back at Oprah Winfrey's best fashion moments from over the years, many can be traced back to one designer: Vera Wang. Their longstanding relationship has made for some sartorial magic, seen everywhere from the Oscars red carpet to the front row of New York Fashion Week to the the Legends Ball, a three-day event Winfrey hosted in 2005 that honored 25 pioneering Black women. 

For the titular white-tie ball, the multi-hyphenate opted for a stunning off-the-shoulder Vera Wang gown in a bright, cherry-red hue that stood out among the crowd, accessorized with dazzling hanging earrings and a glossy red lip. The style must be a favorite of Oprah's, as she wore another Vera Wang original inspired by it on the December 2013 cover of O, according to Huffington Post, and then lent the original to the Smithsonian as part of an exhibit at the National Museum of African American History and Culture a few years ago, titled "Watching Oprah: The Oprah Winfrey Show and American Culture." 

Scroll to Continue

Recommended Articles

Whether or not you have a red carpet on the books, consider shopping red dresses inspired by Oprah in the gallery below.

Please note: Occasionally, we use affiliate links on our site. This in no way affects our editorial decision-making.

Never miss the latest fashion industry news. Sign up for the Fashionista daily newsletter.