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Jessica Diehl

Stylist; Former Creative Director, Vanity Fair

The former Vanity Fair staffer styled transgender TV star Caitlyn Jenner for Annie Leibovitz's cover shoot, which went viral.


Jessica Diehl is the stylist and creative director behind Caitlyn Jenner ’s Vanity Fair cover shoot – arguably the most memorable magazine cover of 2015. Diehl has been highly celebrated for the cover’s huge contribution to fashion’s discussion of the transgender community. In Diehl’s role at Vanity Fair she is responsible for styling all cover shoots and is responsible for all celebrity shoots featured in the publication.

Diehl’s fashion career began as a model, walking the shows for one season in Paris. While modelling wasn’t for her, she did discover she had a real interest in the fashion industry and began interning in the fashion cupboard at American Marie Claire where she stayed for seven months. After a brief stint at Allure magazine, Diehl returned to Marie Claire working under Carlyne Cerf de Dudzeele. When her contract was terminated, Diehl’s hair stylist friend, Didier Malige, introduced her to his girlfriend, American Vogue’s creative director, Grace Coddington . After Coddington’s assistant left, she hired Diehl immediately.

Diehl went on to work at American Vogue for six years, three years as Coddington’s assistant and three as sittings editor. Her big break at the magazine came when she styled a story with Alicia Keys and photographer Norman Jean Roy. When Coddington encouraged Diehl to leave American Vogue to push her career forward, she introduced Diehl to Michael Robers — former Fashion and Style Director of Vanity Fair — who offered Diehl a job as style director at the publication. When Robers left the magazine, Diehl took over his role. During her tenure at the publication, she focused on the magazine’s high-profile celebrity shoots.

Diehl became Vanity Fair's creative director in 2017, but in March 2018 it was announced that she would be departing the publication just 12 months into her new role.

She is represented by Streeters.


Vanity Fair Magazine

Vanity Fair Magazine

2006 - 2018

New York, United States



New York, United States

Vital Statistics



United States
Member since

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What is The BoF 500?

The people shaping the global fashion industry, curated by the editors of The Business of Fashion, based on nominations and on-the-ground intelligence from around the world.