Consistently ranked as one of the richest and most powerful women in the world - even credited with giving President 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 fairly dramatically over the years. But 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!
Check out some of her notable looks through the years in our gallery below.
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?