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Guess the Dress! What Caitlyn Jenner Should Wear to the 2015 ESPY Awards … - E! Online

July 11, 2024 / no comments, on Work day casual wear

James White for E!

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There’s no doubt that Caitlyn Jenner will stun at the 2015 ESPY Awards on July 15, but the question remains: What is she wearing?!

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Michael Kors
This seamless, glittering column gown from Kors’ fall 2015 collection could be, well, a no-brainer for Caitlyn (we can see her wearing it in gold, too).

(Last month, Caitlyn Jenner chose to identify publicly as a woman and E! News will refer to her using female pronouns. In stories published before this date, she was referred to as Bruce Jenner and male pronouns were used.)

Jenny Packham, Catwalking/Getty Images

Diane Von Furstenberg
Caitlyn loves her some DVF wrap dresses, so we wouldn’t be surprised if she went to the source for a custom, waist-cinching design. This floral-print gown is the right silhouette, although we can imagine Caitlyn sporting it in a solid color.

Francois Durand/Getty Images

Ralph Lauren
This one-shoulder Ralph Lauren gown (from the designer’s spring 2015 collection) wafted down the runway and into our imaginations for Caitlyn. And green is the color of rebirth, right?

Catwalking/Getty Images

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Zac Posen
The E! star often opts for effortless black dresses, which is why a sweeping, chromatic gown could be the key for her ESPYs appearance—and it doesn’t hurt that the yellow peek-a-boo sleeves on this resort 2016 number add a bright burst of color. We also love a slim-fitting, iridescent gown from Posen’s fall 2015 collection.

Victor VIRGILE/Gamma-Rapho via Getty Images

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Victor VIRGILE/Gamma-Rapho via Getty Images

Caitlyn will be honored with the Arthur Ashe Courage Award at the ceremony, which means, well, all eyes on her. The star, who has been spotted in clingy wrap dresses, elegant LBDs and her staple sling-back pumps in recent weeks, will arrive to the Microsoft Theater in Los Angeles for what is essentially her red carpet debut. Cue the gorgeous gowns!

Donna Karan

Jenny Packham
While we love all the dresses on our list, these Jenny Packham stunners—a plunging, metallic resort 2016 gown and silver spring 2015 confection—might be our frontrunners.

Donna Karan
We know that Caitlyn is a Donna Karan fan from her Vanity Fair cover shoot (she kept a crimson DKNY dress as a chic keepsake) which is why we can picture her in a slinky, one-shoulder fuchsia number from the designer’s resort 2016 collection.

Catwalking/Getty Images

While the options for Caitlyn seem endless, we can make a few educated guesses—so we’ve assembled a roundup of designer dresses fit for the 65-year-old LGBT advocate. These eye-catching numbers were made for someone beautiful inside and out, so naturally we handpicked them for Caitlyn.

Randy Brooke/WireImage

Zuhair Murad
Caitlyn is sure to pull out all the stops for her big red carpet moment—leading us to believe that something like this show-stopping, garnet-hued Zuhair Murad dress (from the designer’s fall 2014 couture collection) will be her go-to gown.

Frazer Harrison/Getty Images for Mercedes-Benz Fashion Week

Badgley Mischka
This ruby red confection (from the designers’ recent fall 2015 showing) is Caitlyn to a T: The elegant satin finish and bejeweled waistline make for a very strong contender on our predictions list.

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Catwalking/Getty Images

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Monique Lhuillier
While we sort of instinctively want Caitlyn to go for gold on the red carpet—we think a marigold-hued dress would do the trick too. This lovely Monique Lhuillier fall 2015 number might be perfect.

Ralph & Russo
This champagne-hued gown—from the brand’s fall 2015 couture collection—would wow on Caitlyn’s statuesque figure.

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