Living her truth as the most famous transgender woman in the world, Caitlyn Jenner has been out on the town looking utterly gorgeous—and cultivating her personal style in the process. Gravitating towards classic, form-fitting silhouettes, she's the epitome of effortless glamour and we're celebrating each and every look.
In Los Angeles in a perfect LBD and black jacket.
Leaving LAX, Jenner sported a chic all-black airport look accessorized by oversized sunnies and a cream-colored leather jacket by Vince.
Looking like a swinging sixties babe, Jenner went out for lunch in a print mini-dress and accessorized with sleek oversized shades.
For a movie night in L.A., Jenner was appropriately casual-chic in booties, distressed denim and an adorable chunky knit sweater from Intermix—made even cuter by strategically placed shoulder cut-outs.
To support her daughter Kendall as she made her Victoria's Secret Fashion Show debut, Jenner complemented the evening's skin-is-in theme with a super-sheer paneled LBD and suede pumps.
While making a quick Jamba Juice run with a friend in Los Angeles, Jenner offered proof that you can never go wrong in all black.
While celebrating her 66th birthday, Jenner slipped into a black bodycon shift dress, accessorizing with peep toe pumps and an embellished clutch. It was a classic look for the Logo-TV-sponsored fête, during which her squad (including rumored flame Candis Cayne) brought her a cake and sang happy birthday.
On a movie date with a friend, Jenner got all dressed up donning a sequined blouse, slim-fit pants, and black sandals.
For a lunch date with her daughter Kylie, she wears a peach-hued top, frilly white skirt, and strappy sandals.
Jenner was giving us serious Jackie O vibes in her oversized square frames, pussy bow striped blouse, white pants, and T-strap sandals. So what if she's wearing white after Labor Day?
During a Starbucks run, she wears a cleavage-baring navy blue dress, accessorizing with a brown leather shoulder bag and gold sandals.
While embracing her daughter Kendall, Jenner looks red-carpet ready in a tried-and-true LBD.
For an evening out to dinner in Hollywood, Jenner dons this beautiful Solani "Aurelie" Crepe jumpsuit boasting a classic sweetheart neckline.
Jenner was enjoying that Summer Friday feeling at the Fours Seasons Hotel in Westlake Village, CA. The I Am Cait star was all sunshine and smiles in a lightweight sweatshirt and navy-and-white striped maxi skirt.
While shooting a scene for her new docuseries I Am Cait, Jenner hit the town in a leather bodycon wrap dress and strappy heels.
Proving her versatility from glam to classic to edgy, Caitlyn Jenner heads out to dinner in Los Angeles wearing an all-black ensemble complete with leather pants and knee-high boots.
On the heels of her tear-inducing speech at the ESPYs, Jenner hit the races at Del Mar's Opening Day wearing a print orange dress and an oversized, ribbon-trimmed sun hat.
For a lunch date with her daughter Kendall, Jenner opts for a dressier outfit in a black wrap top, floral appliqué skirt, and sleek ankle-strap sandals.
Hitting the Great White Way for a Broadway show, Jenner dons a lacey royal blue wrap dress and slingbacks.
Jenner hits the Patricia Field store in NYC and leaves wearing a completely different outfit, including this eye-catching rainbow sequined mini-skirt. Now that's a total Sex and the City moment.
Channeling an Old Hollywood movie star, she looks totally glam in a figure-hugging leopard print wrap dress while in NYC.
Talk about a perfect LBD—for dinner in downtown NYC, she shows off her curves in a black bandage dress by Hervé Leger and pointed-toe slingbacks.
She dons a classic black wrap dress, black sandals, and a snakeskin clutch while out and about in NYC.
The reality star paired a belted white top with a matching skirt, both boasting a textured white overlay, while at a Gay Pride party in NYC.
While posing with her famous Vanity Fair cover aside her facial feminization specialist Dr. Harrison Lee, she wears a breezy white blouse and jeans.
While hosting a dinner surrounded by beautiful women like herself, she wears a billowy floral print blouse, cropped denim, and sandals.