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Caitlyn Jenner’s 10 Hottest Looks Since Transitioning

Sophia Hutchins, in a sheer black dress, stands with Caitlyn Jenner who wears a sparkly white dress.
Source: Shutterstock

Feb. 6 2020, Updated 5:42 p.m. ET

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It takes more courage and inner strength than most people could dream of having to transition into your true self, and Caitlyn Jenner displayed her confidence when she stepped into the public spotlight in April of 2015. Already a famous face from her Olympian days and Keeping Up with the Kardashians, Jenner was 64 when she transitioned.

MORE: Caitlyn's Gal Pal Sophia Hutchins Says They've 'Never' Been 'Romantically Involved'

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But despite the intense public pressure, Jenner has kept it together supremely well and has also glammed herself up considerably. For an older woman who’s brand new to the scene, she hit the ground running and has shown us how beautiful she can be time and time again.

MORE: Courteney Cox Reacts To Fans’ Claims She Looks Like Caitlyn Jenner

Take a dive into the gallery, and have a look at Jenner’s ten hottest looks since transitioning.

1. Jungle Princess.

Wearing a short red dress, Caitlyn Jenner shows off her long legs as she stands with fellow castmates of 2019’s I’m A Celebrity Get Me Out Of Here.
Source: Shutterstock

In December 2019, Caitlyn Jenner was a seventh-place runner up in the U.K.’s I’m a Celebrity... Get Me Out of Here series. She had also appeared in the U.S. version of the show pre-transition — in 2003 — where she placed fourth.

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2. Roasted.

Caitlyn Jenner wears a black dress while on the red carpet.
Source: Shutterstock

Jenner showed off her curves in an LBD on the red carpet of the Comedy Central roast of Alec Baldwin. But as good as she looked, daughters Kylie and Kendall weren’t happy according to one insider, “Kendall and Kylie in particular can’t understand why she’s being so over the top and cringeworthy. Cait loves the attention though, and she doesn’t give a hoot what her kids or anyone else thinks!”

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3. Oscars.

Sophia Hutchins, in a sheer black dress, stands with Caitlyn Jenner who wears a sparkly white dress.
Source: Shutterstock

Jenner turned many heads with her glittery dress that she wore to the Vanity Fair Oscar Party in Los Angeles in 2019. She’s pictured here with close friend Sophia Hutchins.

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4. Real Love.

Caitlyn Jenner wears a black dress with fur-lined sleeves.
Source: Shutterstock

Jenner wowed the paparazzi in this simple black dress with fur-trimmed sleeve cuffs. This was for the Real Love: Relationship Reality TV’s Past, Present & Future panel in Beverly Hills.

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5. Real Variety.

Caitlyn Jenner poses in a black dress in front of a car, and alongside Sophia Hutchins who wears a sheer grey dress.
Source: Shutterstock

Jenner slipped into an off-the-shoulder black dress that accentuated her long legs for the Variety and Women in Film Pre-Emmy Party. Her lacy sleeves added a touch of va-va-voom to her outfit.

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6. Icon.

Caitlyn Jenner stands on the red carpet in a black outfit with matching black and white clutch.
Source: Shutterstock

Jenner wore a simple, elegant and understated black dress and accompanying black jacket to Harper’s Bazaar ICONS party during New York Fashion Week in September of 2018. She accessorized with a black and white clutch.

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7. Fashion Week.

Caitlyn Jenner, in a floral print dress, takes a selfie of her and Coco Rocha who wears a pink sweater accentuated with black leather.
Source: Shutterstock

No wonder Jenner took a selfie of herself with Coco Rocha — because when you look that stylish you want to remember it. Jenner wore a black and white polka dot dress while at the Jeremy Scott Runway Show in New York.

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8. Vanity Fair.

Caitlyn Jenner wears a figure-hugging red dress with flared sleeves.
Source: Shutterstock

Jenner took to the Vanity Fair Oscar Party red carpet in a resplendent red dress with flared sleeves. She added a simple silver clutch to her outfit that read Caitlyn.

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9. Portrait.

Caitlyn Jenner sits on a stool while wearing a white skirt, black top, and black jacket.
Source: Shutterstock

Jenner sat for a portrait session in 2017. She wore a white skirt, black top and a black jacket with big white buttons looking understated, elegant and beautiful.

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10. Elton John Bash.

Caitlyn Jenner, in a striped burnt peach dress stands next to Andreja Pejic who wears a white dress with black trim.
Source: Shutterstock

Jenner took to the red carpet for the Elton John AIDS Foundation Academy Awards Viewing Party in 2017 in a gorgeous dress that showed off her curves. She posed alongside transgender model Andreja Pejic.

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