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35 Oprah Winfrey Dresses & Skirts Looks

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 Off-the-Shoulder Dress

Off-the-Shoulder Dress

Oprah Winfrey

Oprah Winfrey looked voluptuous in a body-con blue off-the-shoulder gown by Badgley Mischka during the SAG Awards.

 Pencil Skirt

Pencil Skirt

Oprah Winfrey

A black pencil skirt was a classic choice for Oprah Winfrey especially when paired with a fitted blouse.

 Cocktail Dress

Cocktail Dress

Oprah Winfrey

Oprah Winfrey looked retro-chic in a ruched pastel-blue dress during a visit to the CBS Studios.

 Off-the-Shoulder Dress

Off-the-Shoulder Dress

Oprah Winfrey

Oprah Winfrey was all about glamour at the Academy Awards in an off-the-shoulder gown with a black bodice and a glittery ombre skirt.

 Beaded Dress

Beaded Dress

Oprah Winfrey

Oprah Winfrey looked ultra sophisticated at the 2010 Kennedy Center Honors in a beaded column gown.

 Off-the-Shoulder Dress

Off-the-Shoulder Dress

Oprah Winfrey

Oprah Winfrey went for classic sophistication with this pink off-the-shoulder dress during her show in New York.

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah Winfrey chose a stylish dark green gown with a curve-hugging bodice and a flared skirt for the Critics' Choice Awards.

 Cocktail Dress

Cocktail Dress

Oprah Winfrey

Oprah Winfrey played up her voluptuous figure in a shirred navy dress at the premiere of 'Beyonce: Life is But a Dream.'

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah Winfrey looked divine in a green silk evening dress while visiting the Leadership Academy for Girls.

 Long Skirt

Long Skirt

Oprah Winfrey

Oprah Winfrey wore a pretty ensemble on her 'Ultimate Australian Adventure' show, consisting of a long white skirt and a loose pink blouse.

 Cocktail Dress

Cocktail Dress

Oprah Winfrey

Oprah wears a Victoria Beckham nude toned dress when she receives her award at the Maria Shriver Women's Conference.

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah wore a burgundy wrap dress to the screening of 'Precious.' She completed her look with a sleek ponytail.

 Cocktail Dress

Cocktail Dress

Oprah Winfrey

Oprah showed off her glamorous side with this bright grape long-sleeve dress.

 Cocktail Dress

Cocktail Dress

Oprah Winfrey

Oprah was dressed in gorgeous '60s style for a show taping to surprise military families with gifts. Amazing!

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah Winfrey donned a rich red off-the-shoulder evening dress for hosting An Evening With Ralph Lauren in NYC.

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah looks divine in a red orange floor length gown with a button up bodice.

 Empire Gown

Empire Gown

Oprah Winfrey

Oprah Winfrey looked stunning in a ruffled navy gown with cascading ruffles and a sequined bodice.

 Cocktail Dress

Cocktail Dress

Oprah Winfrey

Oprah Winfrey looked fab in her figure-flattering gray cowl-neck dress at the Women in Entertainment Breakfast.

 Knee Length Skirt

Knee Length Skirt

Oprah Winfrey

Oprah Winfrey added major sparkle to her look with a sequined black skirt at the Rock and Roll Hall of Fame Induction Ceremony.

 Little Black Dress

Little Black Dress

Oprah Winfrey

Oprah Winfrey looked more like she was walking the red carpet than filming a movie with this elegant ruffle LBD.

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah Winfrey looked regal in a plum-colored evening dress with a beaded waist and neckline during her 'Farewell Spectacular.'

 Long Skirt

Long Skirt

Oprah Winfrey

Oprah Winfrey teamed a flowing black skirt with a wrap top and a corset for the Kennedy Center Honors.

 Evening Dress

Evening Dress

Oprah Winfrey

Oprah Winfrey showed off her navy evening dress while attending the Annual Academy Awards.

 Shirtdress

Shirtdress

Oprah Winfrey

Oprah Winfrey looked super stylish on the 50th anniversary of the Alvin Ailey American Dance Theater in an iridescent rust-colored shirtdress.

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