Caitlyn Jenner's Best Looks

The I Am Cait star dazzled in a sequin Donna Karan dress at the 27th Annual GLAAD Media Awards on May 14, 2016 in New York City.

Caitlyn Jenner turned heads when she stepped out in a royal blue, off-the-shoulder Moschino Couture! by Jeremy Scott gown for Glamour's Women of the Year Awards in New York City on Nov. 9, 2015. The I Am Cait star was recognized as one of the magazine's Women of the Year for her work within the transgender community.

In one of her first red carpet appearances, Caitlyn rocked a clingy velvet dress. The I Am Cait star made an appearance at Logo TV's Beautiful As I Want To Be web series launch party at The Standard Hotel in Los Angeles on Oct. 27.

Caitlyn looked chic yet comfortable when she went to an L.A. movie theater in a cobalt wrap dress and strappy gold sandals on Sept. 21. And those sunglasses? So '60s movie star!

The reality star looked every bit the rockstar when she took the stage at L.A.'s Greek Theatre to introduce the Culture Club concert on July 24. Caitlyn paired a leather jacket with a gray t-shirt dress and gold accessories for the performance.

Not only did Caitlyn's inspirational speech wow at the ESPY Awards on July 15, her gown did, too! The former Olympian stunned in a gorgeous white Atelier Versace gown that celebrity stylist Jen Rade told ET was chosen for it's "old Hollywood glamour."

Caitlyn wowed in the first promotional photo for her upcoming reality show, I Am Cait. The former Olympian is seen in a floor-length black dress complete with a gorgeous lace backing. She pulled together her classy look with a messy updo and elegant accessories.

Caitlyn flashed a bit of cleavage when she stepped out in New York City on June 30, 2015 wearing a lacy blue dress. The reality star was spotted leaving the Broadway show American In Paris along with her friend, Candis Cayne (not pictured).

The 65-year-old walked out of New York City's Patricia Field in this sequined, colorful skirt complete with a black blazer on June 30.

She looked fierce in a leopard wrap dress as she arrived to Patricia Field in New York City's Soho neighborhood on June 30.

Caitlyn stepped out in a Herve Leger black bandage dress with a pair of black pumps while enjoying a night on the town on June 29.

During Gay Pride weekend in New York on June 28, Caitlyn kept it simple with a white shirt, small belt and a white knee-length skirt with black accents.

For Father's Day, Caitlyn and her family went off-roading, where she wore a loose-fitted, button-up long, white dress with a neutral belt but had a pop of color with her orange hue sandals.

Caitlyn rocked a pair of tight jeans in the rain on June 13 and paired them with a fitted-black blouse, black knee-high boots and an Elisabeth Weinstock Tokyo cross-body bag when she gave a motivational speech to transgender youths in L.A.

When Caitlyn was first introduced to the world via her Vanity Fair cover, she wore a white bustier to show off her amazing assets.