Kris Jenner and Kim Kardashian are both helping Bruce Jenner with his new makeover as a woman, a carefully crafted look he is expected to debut sometime in early July.

The New York Daily News reports the transgendered father of 10 and his team of handlers are being certain to pay close attention to all the intimate details and part of their overall plan is the 65-year-old Jenner agreeing to be on the cover of the summer issue of Vanity Fair magazine dressed as a woman.

The newspaper adds one of Jenner and his associate's biggest concerns is that the former Olympic gold medalist be taken seriously.

"We all saw what happened with the In Touch cover," a source said. "He wants to be taken seriously."

A little more than four months ago, In Touch shockingly ran a photo shopped image of Jenner under the headline, "Bruce's Story: My Life As a Woman." Dressed in a scarf and red top, the photo had Jenner's face and the body of "Dynasty" star Stephanie Beacham.

For the Vanity Fair shoot, Jenner is rumored to be considering taking a page out of Angeline Jolie's playbook and having photographers "accidentally" capture him as he runs errands dressed as "her."

"He will set it up ahead of time and either come out on a normal day -- and from then on he'll be a woman in his daily life for the public -- or he'll go to a dinner and be in a dress," the source added. "But it's likely he'll ease us into the nighttime look."

During his recent 20/20 interview with ABC's Diane Sawyer, Jenner told the host out of all the Kardashian children, Kim Kardashian has been the most understanding of his life change. And her actions now speak louder than his words.

Reportedly, Kardashian has completely "overhauled" her stepdad's closet and turned him "high fashion."

Joked a second source, "When you hang with Kim you have to keep up, and that includes Bruce. No more maxi-dresses for him."