How to clothe an icon? That’s the challenge facing Vanity Fair’s style director Jessica Diehl.


Until recently, Jessica Diehl was the fashion and style director of Vanity Fair. This remains her position, but now she is also The Woman Behind Caitlyn Jenner’s Vanity Fair Cover, a title bestowed upon her by the New York Times and propagated by Google. Diehl, who speaks exceptionally quickly and precisely with a trace of her German upbringing, isn’t reticent on the experience, but chooses her words very carefully; evidently she holds Jenner in great regard and is mindful of what she says. What she does say however is in equal parts moving and fabulous. Beginning with the fact that the project was codenamed ‘Barbra Streisand’.

‘You know what, it’s the dumbest thing I’ve ever come up with in my life, but I tried to think of someone who’s slightly older, and in my head Barbra Streisand is really tall. Obviously she’s not – I couldn’t actually have come up with a worse comparison. But I guess it worked out because no one went from Barbra Streisand to Caitlyn Jenner.’ Magazine covers are usually cloaked in secrecy, but if anything it’s a thin veil, as no one likes to talk quite as much as fashion types. This was evidently quite different, as never before had Diehl overseen a cover that meant quite so much to its subject. Obviously your first Vanity Fair cover is special – as she says, ‘It’s a moment for any woman, but a very specific moment for someone who’s only just introducing themselves as a woman.’


As one might expect, Jessica has had quite a lot of practice making exceptionally famous people look their best, having spent almost a decade at Vanity Fair. Before that she was at Vogue, first working for Grace Coddington and then as an editor, before Grace mentioned she might like to spread her wings a little. So she introduced her to the ‘hysterical, brilliant’ Michael Roberts, then in charge of all things fashion at Vanity Fair, and off she went. Vogue was quite a different proposition to her current title. ‘It’s not so much about fashion... Vanity Fair in my mind, and I think I’m right, has always been much more about image-making.’ Evidently her favourite images to make have involved great characters, rather than the sample-size actresses one might expect. ‘One of my favourites was Jay Z, because it’s not my world, but he’s so fiercely charismatic. I was converted to major fandom after shooting him.’ Mainly, however, she says she can’t remember doing many people, but those she does are in the legendary category. ‘I loved Robin Wright Penn. I love all the boys, of course. I love George Clooney. I can’t help it – he’s a master entertainer. I really liked Lady Gaga.’ Her all time favourite was Lauren Bacall; Jessica says, ‘She was super, like a broad. She was gorgeous, a real character, real proper old Hollywood. And she married Bogey, for God’s sake.’

It was this sort of woman she had in mind for Caitlyn – iconic, ‘proper Hollywood’, timeless. Jessica had a few months to think, and also worry about what clothes she might dress her in. Having had a meeting with Caitlyn, she knew the other woman had put a lot of thought into it too. ‘She’d been thinking about this for decades, and through the decades things evolve. And I think the one thing is, I wouldn’t have presumed to shape anything.’ In Jessica’s mind this meant building the starting elements of an all-American wardrobe. ‘I think if anything I offered a reassurance that chic and simple and stylish American silhouettes can be as empowering as the blingiest Balmain, for example.’ 

Ah yes, outfits perhaps that Caitlyn might have observed in her natural habitat as amiable leader of the Kardashians. ‘You know, she sees fashion as a fun thing, and a dream world in a sense. I mean, can you imagine – you want nothing more than to be a woman, and to dress as a woman, you are a woman... And then you’re surrounded by the hyper version of fashionable women, but you can’t touch it.’ This runway version of womanhood wasn’t what either Jessica or Caitlyn envisioned, however. ‘There’s still in Caitlyn that very American sportswear chic. A classic, Lauren Hutton-esque person. More so than a fashion die-hard.’

This description is pretty apt for Jessica herself, who eschews madly trendy things in favour of Valentino and Céline, and lives in New York with her husband, the English photographer Phil Poynter. In fact, while she thinks trends and runway collections are great, that’s not really what her job’s about. Most designers will create custom gowns for her, and her main focus is ‘that sparkle section’, the part of a show that will make Cate Blanchett or whoever look most luminous. The Vanity Fair experience isn’t some tricky Junya Watanabe, which would make most actresses run a mile. ‘I would hate to look back and say, “Ooh yeah, that’s the so-and-so collection, 1997.”’ The fashion there should be much more about style, and secondary, because it’s about the person.’ With regards to Caitlyn, Jessica says, ‘At the end of the day, it’s about a woman in Vanity Fair, and there are certain expectations there. She wanted to be seen the way she sees herself, in the context of Vanity Fair. And to me that made total sense.’