Oprah in Citizens of Humanity Jeans

10. Cesare Paciotti Sweater and Citizens of Humanity Jeans
During one 2004 taping, Oprah kept it casual in a Cesare Paciotti sweater and Citizens of Humanity jeans. "Oprah used to say 'no jeans after 40,' but we changed her mind," Kelly says. "I think she looked young, fun and still appropriate."
Oprah in Lanvin

9. Lanvin Skirt
This brown leather skirt by Lanvin was one of Oprah's must-have pieces in 2006. Paired with a Valentino sweater and Dolce & Gabbana belt, it was the perfect fall look. "We loved this skirt that season—it was one of her favorites, and so began a great affection for all things Lanvin," Kelly says. 
Oprah in a Mad Men inspired dress

8. Mad Men-Inspired Dress
In 2009, The Oprah Show celebrated the swinging '60s with the stars of Mad Men. Kelly worked with Emmy award-winning costume designer Janie Bryant to design this pink dress for Oprah. "This was such a fun collaboration with the costume designer," Kelly says. "The 1960s silhouette is actually perfect for Oprah's shape."
Oprah in Alexander McQueen Dress

7. Alexander McQueen Dress
In 2006, Oprah asked Senator Barack Obama to come on the show to discuss his vision for the future. "I remember her telling me he could be the next president," Kelly says. "This was a timeless dress." Three years later, President Obama was inaugurated, becoming America's 44th president.
Oprah in TSE and Louis Vuitton

6. TSE Sweater and Louis Vuitton Skirt
Kelly styled Oprah in this soft pink sweater and skirt for her 2005 interview with Tom Cruise. "This show got press for reasons other than her outfit, but I've always thought [the look] was both pretty and feminine."
Oprah in Naeem Kahn Skirt and Sweater

5. Naeem Kahn Skirt and Sweater
Kelly still loves the Naeem Kahn outfit Oprah wore for the 20th season premiere with Jennifer Aniston. "It had a very celebratory feel—just enough sparkle without being too dressed up," she says. 
Oprah in Valentino and Tuleh

4. Valentino Top and Tuleh Skirt
In the past, Kelly says Oprah didn't like to mix different designers within the same outfit—but this Valentino top with pearl accent and sequined Tuleh skirt is her favorite example of designers working in harmony. "I loved these two together," Kelly says. "The fit and flair of the skirt is a great silhouette."
Oprah in Celine

3. Red Céline Suit
The 19th season of The Oprah Show kicked off with one of the biggest giveaways in the show's history—each and every audience member went home with keys to a brand new 2005 Pontiac® G6™. For Oprah's big reveal, Kelly dressed her in a gorgeous red suit by Céline.

"This suit came from an O magazine shoot that was never used but ended up being the perfect thing to wear that day—especially with all those red bows on the key chains," Kelly says.
Oprah in Carolina Herrera

2. Carolina Herrera Tweed Dress
Oprah wore this Carolina Herrera gray tweed dress in November 2009 to announce that Season 25 would be the farewell season of The Oprah Show. "[It was] the ideal dress for that moment—classic and chic," Kelly says.
Oprah in Rachel Roy

1. Rachel Roy Post-Oscar® Dress
In 2007, Oprah wore a gown in a gorgeous shade of merlot to celebrate with Oscar winners like Forest Whitaker and Helen Mirren. "Rachel Roy made it for us, and it looked great onstage," Kelly says. "It was one of those times when everything works together—set color, lighting, hair and makeup and a great dress."