The "I Am Cait" star sported a chic black velvet shift dress for her red carpet debut this week at Logo TV's "Beautiful As I Want To Be" web series launch party in Los Angeles. She paired her elegant ensemble with peep-toe pumps and a silver sequin clutch.
But, it seems she took fashion cues from Oprah Winfrey, who first donned the fancy frock during an appearance on "The Late Show With Stephen Colbert" earlier this month. The media mogul added some edge with black Valentino rock-stud pumps, her signature curly locks and a killer red lip.
While the former Olympian has paid homage to Kate and Oprah, her style icon is actually Angelina Jolie!
During a recent episode of her E! reality show, the 66-year-old called on Angie's stylist, Jen Rade, to help her boost her wardrobe.
"The bottom line is, I really need a professional to coordinate everything. [Jen Rade] does Angelina Jolie and I just love her look. Very casual, very elegant, chic, so I'm dying to meet her," she said.
Rade was responsible for the stunning white Atelier Versace gown that Jenner wore to the ESPYs, revealing that the dress was custom-made for Cait's big night.
"We wanted to do something classic, chic, and sophisticated. I just wanted it to be about her and not let anything take away from that," Rade said at the time.
The dress certainly accomplished all of that and even won Jenner some comparisons to Jolie!
Check out more of Caitlyn's most glam moments above, and let us know who you think won the style showdown by voting inside the gallery at the top.