The Styling Secrets of Rihanna’s Vanity Fair Cover Shoot in Cuba
Vanity Fair fashion and style director Jessica Diehl has dressed many of the biggest stars in the world, playing a critical role in creating some of the most famous images of Caitlyn Jenner, Jennifer Lawrence (and a very-well-behaved snake), Taylor Swift, and others. The secret to her success is that she knows how to dress women in the particular breed of glamour that makes them feel most like themselves.
Still, styling a woman who is as esteemed as Rihanna for her fashion prowess—and in Cuba, mere weeks after the U.S. lifted travel restrictions to the island, no less—is no small task. Diehl spoke to VF.com about how she made Rihanna “Rihanna” for her first Vanity Fair cover shoot, plus tells us the secret to styling a nude.
VF.com: What was the process for pulling together the cover spread? Did you decide to shoot Rihanna, then decide on Cuba?
Jessica Diehl: It all sort of happened at the same time. . . . The minute it was decided that Rihanna would be on our cover, travel restrictions were lifted, so we went straight away. It was sort of a no-brainer.
VF.com: What is the process like styling a shoot for someone who’s so renowned for their sense of style? Is it intimidating, or is it empowering, in a way?
I think whenever you style someone who is known for their style, or their style risks, it’s not so much that it’s intimidating—it’s more that you want to take that into account. Let’s put it this way: if we’re doing a fashion shoot with Rihanna, I probably would have picked different clothes. But it being a Vanity Fair shoot, it becomes very much about making Rihanna “Rihanna” in a way that doesn’t feel pinpoint-able or date-able. So that you don’t look at it and go, Oh, I remember that season, or that trend. It’s much more about Rihanna. The clothes are kind of the supporting actors to the star.
What was the process, then, of creating “Rihanna”?
It’s a combination: you have Rihanna, then you have Cuba, then you have [photographer] Annie [Leibovitz] who loves Cuba, and has photographed lots of things there. It’s taking into account the coloring, and the mood, and the sort of patina of the places and houses and music venues and things like that. It became about what would be, in our imaginary world, believable, because it didn’t feel completely right to go 4,000 percent over the top—we wanted to be part of Cuba, we didn’t want to be outside of Cuba. The clothes . . . felt like something Rihanna would take off the rack herself, like something we could send her out into the street with. If she had been in any way constrained or posing or feeling artificial, none of what we did would have worked, really.
And how collaborative was the effort to find that clothing?
There were conversations with her team about what the feeling and the mood were going to be. And it’s always so very difficult to talk about clothes over the phone; it’s difficult even sometimes to share pictures of clothes, because you don’t know how to judge them because they’re on a model, and you don’t know the fabrication and so on and so forth. We had a lot of conversations about where Rihanna is—or was, at that moment. But it’s very difficult to put into words the creative conversation, because I think if anyone actually listened to it they would all think we’re crazy. So we had several creative conversations about color and feeling and the idea of it somehow seeming effortless. It’s clearly not a fashion show; it’s simply Rihanna in Cuba.
How did you develop the mix of designers, which includes Ralph Lauren, Dior, and Valentino, but also, for example, the lesser-known designer Carine Gilson?
Carine Gilson is probably one of the most talented lingerie designers—she’s Belgian—who uses incredible, incredible Belgian lace and silks, and her colors are amazing. Because Cuba was about color, the red that she had, bizarrely, was the exact red of this kind of bar in some hidden corner in Havana. There was really no other way than to shoot it. And Rihanna is not someone who’s a slave to designer brands. She’ll go and put on whatever she likes. Whether that’s Dior or a smaller brand, she knows good fashion, and takes risks and tries out different designers and has fun with it.
Did you see the Dior trench and panties look and look on the runway and think: Rihanna? Or was it only when you were pulling things for the shoot that it came to you?
It was really putting together the shoot. But that picture, specifically, is very much her mega-star status on display: she’s still very irreverent, and she does things her own way. I don’t think that look is necessarily what you think of when you think of Dior. And much like Rihanna herself, it’s just good, so it works in all kinds of different ways. And that’s kind of how she is. She can put on, I don’t know, a sneaker, and make that a whole different thing somehow. I don’t know how she does it.
How did you land on the leopard Manolo Blahnik mules for the nude photo?
There’s something about Manolo Blahnik shoes that whatever the trend is, was, will be, they’re kind of the epitome of a feminine, beautiful, and alluring kind of shoe. And there’s something about leopard print, when done right, that’s just very evocative of a tiny bit of danger. And it felt not as oppressive as a pump. You can believe that Rihanna would be in a mule and would plop herself down on a bed in the most alluring kind of fashion, whereas if you have a pump on, that would be kind of posed and contrived. And a Manolo is so timeless, and in those kinds of images that Annie does, you want to look at it in another 15 years, and you don’t want people to think, Oh, remember when platforms were happening?
Can you tell us about “styling” a nude shoot?
It’s always very funny to me when it says “styling by!” This was a vision that Annie wanted to make happen because there’s a purity. And you know when it comes to styling a nude, you just have to practice restraint. That’s really what it’s about: restraint, and not wanting to put any kind of stamp on it. That I got to put a shoe on I’m very happy about—and that I restrained myself from junking it up with jewelry. That would have also been beautiful, but it would have been a very different picture.
The colors in the cover image have great harmony—was it a big effort to bring all of those blues together?
We’d gone so far and done a red on red, but we loved the sort of turquoise-y color of the little jumpsuit—which is actually a Valentino couture underpinning that had a very, very beautiful tulle long skirt over it. But we wanted to see some Rihanna skin and legs and tone and all that.
But it was one of those rare moments where there was no prior agenda. It was everybody looking at the locations, looking at her, looking at the light, looking at the people, and thinking, This could work. And it had to be something that she felt comfortable in: what you don’t see in the cover is that there are hundreds of people around. Hundreds. . . . It was quite intimidating and shocking, the amount of fan crowds she draws. She needed to be in something that she could be 360 degrees of Rihanna, from all angles, because everybody had a smart phone. Then we just found a place where that worked, but it certainly wasn’t something that was conceived around the outfit.