Oprah

Over the past 25 years, Oprah has worn just about every trend imaginable. From her high hairdos...
Oprah's shoes

...all the way down to the soles of her designer shoes.
Oprah's shoes

Despite what some viewers may think, Oprah's shoes weren't always red carpet worthy. "During the commercial break, an audience member asked me why I was wearing these ugly shoes," Oprah said during one show taping. 
Oprah

From the patterned power suits of the '80s...
Oprah

...to some "revealing" outfits. "When you see my armpits, you're supposed to," Oprah said. 
Oprah

One thing Oprah learned for sure—bigger isn't always better.
Oprah's holiday sweater

The holidays always brought out the most festive fashion don'ts.
Oprah's missing earring.

Wardrobe malfunctions happen to the best of us but few have to explain them on national television. Notice anything missing in this picture? "I dropped my earring!" Oprah said.
Oprah dressed up a Diana Ross.

There was also the occasional misguided makeover, like when Oprah dressed up as one of her idols, the legendary Diana Ross. "I feel like a drag queen right now," Oprah said. 
Oprah in her Tina Turner wig.

But, of all the regrettable trends, Oprah's beloved Tina Turner wig was her absolute favorite.
Oprah in her Tina Turner wig.

"Truth be told, I planned on wearing [the wig] on the show once with Tina," Oprah says. "Then, I kept wearing it and wearing it some more...and wearing it again." 
Oprah in her Tina Turner wig.

Finally, Stedman became the voice of reason. "Stedman came to me and said, 'When is somebody going to tell you?" Oprah says. "I said, 'Tell me what?' And he said, 'You are not Tina Turner.' I said, 'No, but everybody really likes this wig.' He goes, 'Everybody is lying to you.'"

Oprah says she gave the Tina wig to her cousin Alice, who wore it for years. Oprah's producers called Alice to try to track down the wig, but Alice said she gave it to her friend Ruby. "We called Ruby, and Ruby said she put it in a box, and she doesn't know where that box is," Oprah says. "So anyway, it's gone."

Look back at 22 Oprah hairstyles