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27 Times Caitlyn Jenner Served Up Some Seriously Chic Style

Living her truth— and looking good while she's at it.

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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.

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1 of 27
January 7, 2017

In Los Angeles in a perfect LBD and black jacket. 

2 of 27
December 18, 2015

Leaving LAX, Jenner sported a chic all-black airport look accessorized by oversized sunnies and a cream-colored leather jacket by Vince.

Clothing, Eyewear, Leg, Glasses, Sleeve, Human leg, Shoe, Shoulder, Sunglasses, Dress,
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3 of 27
December 8, 2015

Looking like a swinging sixties babe, Jenner went out for lunch in a print mini-dress and accessorized with sleek oversized shades.

4 of 27
November 27, 2015

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.

Clothing, Trousers, Coat, Dress, Shoe, Outerwear, Formal wear, Suit, Suit trousers, Fashion,
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5 of 27
November 10, 2015

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.

6 of 27
October 30, 2015

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.

Shoulder, Dress, Joint, Style, One-piece garment, Flooring, Fashion, Fashion model, High heels, Premiere,
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7 of 27
October 27, 2015

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.

Clothing, Brown, Sleeve, Shoulder, Textile, Joint, Style, Street fashion, Pattern, Fashion accessory,
8 of 27
October 17, 2015

On a movie date with a friend, Jenner got all dressed up donning a sequined blouse, slim-fit pants, and black sandals.

Clothing, Eyewear, Footwear, Leg, Vision care, Glasses, Sunglasses, Textile, Human leg, Outerwear,
9 of 27
October 5, 2015

For a lunch date with her daughter Kylie, she wears a peach-hued top, frilly white skirt, and strappy sandals.

10 of 27
October 3, 2015

Speaking at the Point Foundation's fourth annual Voices on Point dinner in Los Angeles, Jenner serves up some monochromatic magic in a red hot pantsuit.

Clothing, Eyewear, Tire, Wheel, Vision care, Automotive tire, Sleeve, Alloy wheel, Trousers, Shoulder,
11 of 27
September 28, 2015

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?

Clothing, Eyewear, Glasses, Dress, Shoulder, Joint, Human leg, Style, Street fashion, Sunglasses,
Splash News
12 of 27
September 22, 2015

During a Starbucks run, she wears a cleavage-baring navy blue dress, accessorizing with a brown leather shoulder bag and gold sandals.

Nose, Mouth, Eye, Hairstyle, Black hair, Strapless dress, Brown hair, Flash photography, Long hair, Chest,
13 of 27
September 8, 2015

While embracing her daughter Kendall, Jenner looks red-carpet ready in a tried-and-true LBD.

Face, Human body, Trousers, Shoulder, Joint, Outerwear, Dress, Coat, Style, Formal wear,
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14 of 27
July 29, 2015

For an evening out to dinner in Hollywood, Jenner dons this beautiful Solani "Aurelie" Crepe jumpsuit boasting a classic sweetheart neckline.

15 of 27
July 24, 2015

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.

Face, Leg, Event, Trousers, Shirt, Dress, Outerwear, Camera, Coat, Video camera,
Splash News
16 of 27
July 18, 2015

While shooting a scene for her new docuseries I Am Cait, Jenner hit the town in a leather bodycon wrap dress and strappy heels.

17 of 27
July 17, 2015

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.

Eyewear, Hat, Leg, Sun hat, Fashion accessory, Sunglasses, Summer, Headgear, Costume accessory, Fedora,
18 of 27
July 16, 2015

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.

Sleeve, Human leg, Shoulder, Joint, Standing, Style, Elbow, Knee, Waist, Street fashion,
19 of 27
July 11, 2015

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.

Leg, Trousers, Coat, Dress, Outerwear, Suit, Electric blue, Cocktail dress, One-piece garment, Blazer,
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20 of 27
June 30, 2015

Hitting the Great White Way for a Broadway show, Jenner dons a lacey royal blue wrap dress and slingbacks.

21 of 27
June 30, 2015

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.

Clothing, Bicycle tire, Bicycle wheel rim, Bicycle wheel, Dress, Land vehicle, Bicycle frame, Shoulder, Bicycle part, Bicycle,
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22 of 27
June 30, 2015

Channeling an Old Hollywood movie star, she looks totally glam in a figure-hugging leopard print wrap dress while in NYC.

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23 of 27
June 29, 2015

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.

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24 of 27
June 29, 2015

She dons a classic black wrap dress, black sandals, and a snakeskin clutch while out and about in NYC.

Microphone, Human body, Entertainment, Audio equipment, Music artist, Singing, Pop music, Fashion, Singer, Song,
25 of 27
June 28, 2015

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.

Arm, Human, Leg, Glasses, Eye, Human body, Hand, Hat, Mammal, Sitting,
26 of 27
June 10, 2015

While posing with her famous Vanity Fair cover aside her facial feminization specialist Dr. Harrison Lee, she wears a breezy white blouse and jeans.

Flowerpot, Tree, Leisure, Tourism, Summer, Interaction, Bag, Luggage and bags, Houseplant, Handbag,
27 of 27
June 6, 2010

While hosting a dinner surrounded by beautiful women like herself, she wears a billowy floral print blouse, cropped denim, and sandals.

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