Oprah Winfrey Fashion Transformation

Twenty Years of Beautiful at Any Size
Consistently ranked as one of the richest and most powerful women in the world -- even credited with giving President-elect Obama over one million votes -- Oprah Winfrey has indeed risen to heights heretofore thought unimaginable. As with all of humanity, though, Oprah has had one very persistent and public struggle, and that is with her weight, which has fluctuated through the years, unlike her meteoric star. As we chronicle her looks over a 20-year period, you'll see that Winfrey remains smart about choosing styles that compliment her figure at any size. There should be NO shame in her game!

Text by Hayat Mohamed, Photo editor, Denyse Clarke

Oprah Winfrey Fashion Transformation

November 1988
In 1988, two years after the debut of her highly successful talk show, Oprah was at her lowest weight ever, dropping an astounding 68 pounds. Who could forget the day she unveiled her new figure on 'The Oprah Winfrey Show' along with a wagon carrying 68-pounds of fat?

Oprah Winfrey Fashion Transformation

January 1991
Three years after her amazing weight loss, Oprah fell off track and packed on some extra pounds. Her petite figure was history at in 1991 at the Daytime Emmy Awards, of which the undisputed talk show queen has won many.

Oprah Winfrey Fashion Transformation

May 1994
"Three" seems to be the magic word for Oprah -- or maybe "corsets"... At the 1994 Emmy Awards, the media mogul showed off a tiny waist and sculpted arms in a form-fitting dress.

Oprah Winfrey Fashion Transformation

May 1995
A failed diet regimen or a poorly-cut dress? Whatever the reason, it appeared that Ms. Winfrey's Emmy count wasn't the only thing climbing that year. When she received her award at the Daytime Emmy Awards her hips appear to have widened noticeably from the year before. She still stands triumphant.

Oprah Winfrey Fashion Transformation

February 1996
Ms. O's waistline was looking rather slim at the 68th Academy Awards in a navy blue fitted satin gown in 1996. Eleven years prior, Winfrey was nominated for an Academy Award for her role as Sophia in 'The Color Purple.' Since then, she has starred in and produced several films.

Oprah Winfrey Fashion Transformation

September 2003
Oprah arrived to the 54th Annual Primetime Emmy Awards in 2002 in a mellow yellow dress and her constant companion Stedman Graham, her man since 1986. Despite the added weight she was simply radiant on the red carpet. There goes that corset again!

Oprah Winfrey Fashion Transformation

January 2003
In 2003, Oprah managed to stabilize her weight. Maybe it's the slimming choice of black but she looked as if she had dropped a few pounds when she was spotted attending the American Auction at the Metropolitan in NYC.

Oprah Winfrey Fashion Transformation

February 2003
A month later, Ms. Winfrey was looking pretty fierce on the red carpet of the Association of American Publishers Honors Awards in a clingy red dress. By the looks of it, O was definitely hitting the gym.

Oprah Winfrey Fashion Transformation

August 2004
The year 2004 rang in a new do and a new waist for Oprah. She had no problem strutting her stuff at the National Underground Railroad Freedom Gala. Forget the color black, we give props to Oprah's diet and fitness plan.

Oprah Winfrey Fashion Transformation