
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.




Comments: (4)
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By: Rene on 5/24/2011 10:40PM
That is a powerful black woman! Self made! Awesome!These are our examples for all little AA girls you can be what you espire to be. Michelle Obama another powerful black woman class, poise, educated Black Girls Rule!
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By: Barbartton sitn on 5/25/2011 2:12AM
he kind of looks like a hott bag lady. some things are over sized or ill fitting but they look good.
http://digwin.com/user/Barbartton/profile
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By: ZZ on 5/25/2011 10:51AM
Oprah reminds me of my deceased aunt. She knew her size and wouldn't dare let anyone talk her into wearing anything unflattering to her hips etc. My deceased friend had a joke "I love when Summer comes because big black women put on stuff they know they shouldn't and I can enjoy all the jiggling like jelly!" hahaha Even Barbara Walters asked O about those uncomfortable looking shoes. I know I know even my mom says certain dresses/skirts demand a heel!
Can we please tell black women after a certain age don't wear corn rolls (braided hair) styles I used to put on my girls when they were in grade school? Geesh.....
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By: LoveSexy on 5/25/2011 6:32PM
No matter what size Oprah is beautiful, awesome, and a powerful Black lady. Love her and wish her well.
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