For an event as big as the annual ESPY Awards, Caitlyn Jenner is definitely going big on his stylist, too. She is tapping no less than Hollywood superstar Angelina Jolie's stylist Jen Rade to make her up for that special night.

Jenner will be presented with the notable Arthur Ashe Courage Award at the ESPYs Los Angeles ceremony to be held at the Nokia Theater Wednesday, an award that spun a web of speculation from sports critics and fans alike.

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One of Rade's most memorable "works" was that of the 2012 Academy Awards night where she styled Jolie in that black high-slit Versace dress.

Jenner is relying on Rade for a custom-made dress for the awards and may be going for an ivory gown. They are also looking at after-party outfits. Questions about whether Rade will continue to be styling Jenner even after the event is unsure, a source told US Weekly.  

But the 65-year-old transgender's award did not come without a price. Critics are allegedly questioning Jenner's suitability for such an award.

The ESPY Awards honors individuals with notable athletic achievements. The ceremony is highlighted by three main awards: the Arthur Ashe Courage Award, the Pat Tillman Award for Service, and the Jimmy V Perseverance Award.

ESPN was quick to defend their decision. ESPY producer Maura Mandt told the Sports Illustrated in an interview that Jenner showed "enormous courage and self-acceptance" when he dealt with his identity and bravely came out to the public as a transgender woman.

Mandt also added that Jenner was undoubtedly one of the best athletes of this time and that what he has done "transcends sports."

The ESPY will be Jenner's first public appearance as "Caitlyn," the transgender woman. As this may be one of his biggest nights, the Kardashian siblings and his six biological children are expected to witness the special event. However, Jenner's ex-wives may not be attending, the Daily Mail learned.

TagsCaitlyn jenner, ESPY awards, ESP Awards, Jen Rade, Arthur Ashe Courage Award, ESPY 2015