The picture showed a very slender - looking Winfrey in a dress that was recognized by actress Ann - Margret 's fashion designer .
Oprah Winfrey was on the cover of TV Guide in 1989 .
The picture showed a very slender - looking Oprah Winfrey in a dress that was recognized by actress Ann - Margret 's fashion designer .
Oprah Winfrey was on the cover of TV Guide in 1989 .