Valentino shoes

These gorgeous, glossy pumps with Valentino's signature bow embellishment certainly aren't for everyday wear, but they were just right for kicking off Oprah's 25th season.
Oprah's Dorothy shoes

Oprah calls these sparkly slingbacks her "Dorothy" shoes.

Christian Louboutin's spokeswoman Shawna Rose says this dazzling design was, in fact, inspired by a fantasy world. "Christian likes to play with iconic images," Shawna says. "Every little girl going into womanhood dreams of the Cinderella shoe and the ruby slipper, and that's the personification of that."

Oprah says this is a shoe that can go with anything. "I've worn it with jeans on this show, and I've also worn it out with evening wear," she says. "It's fantastic."
Clu by Jimmy Choos

If you've followed Oprah's feet over the years, you've seen the "Clu" peep-toe shoe by Jimmy Choo. The metallic hue goes with everything, and they've become one of Oprah's favorites.
J.Crew shoes

Not all of Oprah's shoes have designer labels. During Glamorous, High-Flying, Action-Packed Dream Jobs, Oprah was decked out in J.Crew from head to toe—and her favorite piece was her J.Crew shoes. "I have these shoes on and they're so comfortable I can't get over it," Oprah says. "A reasonable heel and a comfortable shoe."

J.Crew's executive creative director Jenna Lyons shares the shoe's secret. "It's all about the interior platform that makes them that much more comfortable," she says.
Oprah's Cole Haan boots

After years of living in pain, Oprah's staff finally said "enough!" They searched high and low to find the ever-elusive comfortable—and cute—high-heeled shoe.

The dream was realized in 2006 when Oprah was introduced to Gordon Thompson, the creative director for Cole Haan shoes. Using Nike technology, Gordon engineered an "air bag" used in heels and boots that provides cushion for the feet. "This is life changing," Oprah says. "It's not a cure for cancer, but it is a cure for your feet!"
Oprah's black and white Louboutins

Oprah loves her Christian Louboutins! These black-and-white peep-toes have been in regular rotation in Oprah's wardrobe for years.
Oprah's green pumps

Once the cameras stop rolling, Oprah kicks back in her army-green heels to chat with the audience and give her feet some relief.
Oprah's leopard-print Louboutins

Leopard-print Louboutins? Yes, please!
Oprah in Manolo Blahnik

Most of us organize our shoes according to style, color or occasion (which pairs are for work, weekends or big nights out). But Oprah also organizes hers by how long she can bear to keep them on her feet. "I've gone to parties wearing shoes that hurt so much, I wanted to come home early," Oprah says. "What fun is that?"

Oprah says this Manolo Blahnik slingback is the perfect heel. “I can actually wear it out of the building, not just between the control room and stage," she says.
Oprah's Prada flats

These flats may not be flashy, but they get a perfect score on Oprah's shoe pain-o-meter. "You know how you used to come home from school and change out of your good clothes?" Oprah says. "Well, these Prada flats are my after-school shoes—cute and comfortable."
Oprah's shoes from Mariah Carey

Music superstar Mariah Carey gave Oprah these sexy silver stilettos.
Oprah's shoes

Oprah says she loves these black-and-tan pumps, but they rate high on her pain-o-meter. "As cute as they are, after wearing them for an hour, my shins hurt so much that I had to go to the doctor!" she says.
Oprah's boots

Oprah stays stylish in the winter months by zipping up a pair of strappy boots.
Oprah's flip-flops

Yes, even Oprah wears flip-flops! She settles back to watch Never Before Seen Oprah Outtakes with the audience in 2006.
Oprah in Jimmy Choo stilettos

Oprah says these black, strappy Jimmy Choos are comfortable to walk in. "The wider toe box gives me more wiggle room," she says.
Oprah's leopard print shoes

Oprah says she can stand in these leopard-print heels for about 10 minutes before she starts feeling the pinch. "Another pretty pair that's strictly for TV—I take them off the minute the show is over," she says.
Oprah's magenta pumps

These magenta peep-toe heels match Oprah's spring tunic perfectly.
Oprah's snake-print Louboutins

Oprah's snake-print slingbacks by Christian Louboutin sizzle onstage.
Oprah's Christian Louboutin espadrille sandal

Christian Louboutin may be known for his sharp stilettos, but his summer sandals are just as fabulous. Oprah shares a laugh with the audience while wearing Louboutin espadrilles with ribbon ties.
Oprah's silver mules

These silver mules look great on camera, but once Oprah's off the air, it's off they go!
Oprah's eBay auction

In 2010, Oprah chose more than 150 items from her closet to auction on eBay to benefit the Oprah Winfrey Leadership Academy for Girls. Her collection included everything from a practical pair of patent wedges to lace-up metallic booties. 

Some of the shoes Oprah parted with were simply too small. For years, she was wearing the wrong size shoe! "I've since learned I wear a size 11, not 10," Oprah says.