A Fascinating New Look at Carolyn Bessette Kennedy

A new book documents her style and career at Calvin Klein in the nineties.

Carolyn Bessette Kennedy never wanted to be famous. Yet she has endured as one of the most significant fashion icons of the last century. More than 20 years after she died at age 33 in the summer of 1999 in a plane crash with her husband John F. Kennedy Jr. and sister Lauren off the coast of Martha’s Vineyard, she remains a nineties legend, locked in a social media exposure loop the way she once was in print tabloids.

In the old images that still circulate, Carolyn’s minimalist style looks as modern today as it was then. Her fashion — at times normcore, almost never bearing a print, and quite often just black — has taken on renewed relevance as labels like Khaite, Bottega Veneta, and The Row attempt to replicate her luxurious simplicity.

Fashion creative director Sunita Kumar Nair knew that those photos of Carolyn were more than content scraps for Instagram lookie-loos — they were impacting what the fashion industry was making. Kumar Nair had seen her photos on inspiration boards for designers like Wes Gordon, and heard from friends who worked with the likes of Marc Jacobs and Bottega Veneta’s Matthieu Blazy that Carolyn influenced their work, too. She heard from a lecturer at Central St. Martins that students still pull Carolyn for mood boards. And she thought there ought to be a book to serve as a reference point for every creative still influenced by her and every consumer still fascinated by her.

Sunita Kumar Nair.

So during the pandemic, Kumar Nair decided to create Carolyn Bessette Kennedy: A Life in Fashion, a book that pays homage to both Carolyn’s style, but also to the fashion-person side of her that gets lost in her legacy.

Born in White Plains, New York, Carolyn grew up in Greenwich, Connecticut and attended Boston University in the eighties. She had talked about moving from Boston to New York with friends before she went for it in 1989. Calvin Klein’s then-president of ready-to-wear Susan Sokol plucked her from a Boston mall, where she was working in one of the brand’s stores, for a sales position in the New York office that involved dealing with celebrity clients. “It was so obvious that she had a great sense of style and stood out from the rest,” Sokol told Kumar Nair.

Carolyn was privately shocked at how quickly these clients could part with thousands of dollars. “We both lived in the East Village, took the same subway to work, went to the same bars and restaurants, and dated the same type of guys — and we were so broke!” Carolyn’s colleague Stormy Stokes told Kumar Nair. “Most of the girls at Calvin had similar long hair, but Carolyn never blew hers out. She taught me how to style my own: wash it, flip it up and down twice, then tie it in a top bun, and ride the subway. By the time we would get to the office, we’d take the bun down and our hair would just be ready to go. Let’s face it, neither of us could afford to have a blowout or dye our hair then, so with these tricks and our clothing allowance, we looked the part.” Carolyn worked her way up to publicist, collaborating closely with Calvin, and, as Kumar Nair explains, influenced many aspects of the brand.

Carolyn Bessette Kennedy: A Life in Fashion is as delicious to read as it is to look at. I loved so many things about this book, from the way the cover feels to the layout to the surprising details it brings to life about Carolyn, like how she loved saying the word baby. (As in, “Baby, that shit doesn’t matter.”) This is an excellent holiday gift and a great addition to any fashion book collection. Ahead, Kumar Nair talks about the book and why Carolyn has endured.

The word “timeless” gets thrown around a lot in fashion, and Carolyn Bessette Kennedy might be one of the few people to whom it truly applies. Can you think of anyone else whose photos look as modern today as decades ago? Other style icons like Jackie Kennedy and Princess Diana – who you note share parallels with Carolyn – look like they’ve been captured at a moment in time.

I agree. I have wracked my brain about this. Say we look at Audrey Hepburn, because she was very clean in her presentation of her looks, it still reads as 1950s and 1960s. I think Samira [Nasr, Harper’s Bazaar editor-in-chief] said, just take Carolyn’s jeans or her shoes, and they're in trend now. I feel if we are looking at someone equivalent for today, the Olsen twins are something of Carolyn in the sense that they dress down, they don't dress up so much, but you know that what they're wearing is very high-end.

Carolyn with her Birkin. Credit: © Henry McGee/ZUMA Wire

I can only imagine how challenging your research process was, including getting her friends to speak publicly about her for the first time.

Close friends of hers who had never spoken before were all a little edgy, to be honest. There's not been great press about her. And people have turned genuine, innocent stories into something that they're not. And I was very sure that it was just going to be about Carolyn in her fashion world and what she means to us today. And when I spoke to her friends, they were completely comfortable talking about that. This was something I think Carolyn was quite genuinely comfortable with. You can sense in the paparazzi pictures that she enjoyed clothes.

What I liked about the book was that it presented her as a career woman, who happened to be working at Calvin Klein at a pivotal time for the brand and for New York fashion. Many people think of her primarily in relation to JFK Jr., so your book felt like it offered a fresh perspective.

I think we forget who she was before John Jr. And I think we make women smaller sometimes when they have married famous people, and don't remember what they did before. She was working closely with Calvin and Kelly [Klein, his then-wife], and there is this kind of toughness you have to have as a person to work with people like that. Speaking to her friends and her colleagues, I learned more about Carolyn the working woman — and that she was always working. Even though people painted her as coming from a quite privileged background, she came to New York and had to make her rent. There aren't many people who survived the fashion world then, and she was one of them.

Before she met John, she didn’t own sneakers, according to Kumar Nair’s book. © Globe Photos/ZUMA Wire

What was it like to work for Calvin Klein in New York at that time? I loved the detail you had in the book about how nail polish was verboten in the office because it wasn’t considered on-brand.

You were either a Calvin girl or a Ralph [Lauren] girl or a Donna Karan girl. They all shared the same building at one point, and you would know who worked for who in the lift from the way that they dressed. It wasn't just about fashion. It was something more lifestyle-y as well. There are the Calvin Girls, what are they doing? Where are they going out? Kate Moss was his model, but the women who worked for him reflected that same coolness.

Carolyn didn’t want to be famous, right? I think that’s part of her enduring appeal today — she was never out to be Kim Kardashian.

More than two friends told me that John Jr. asking her to marry him was a real inner conflict for her. She was known in her Calvin Klein days for being very private. Friends who thought that they had known her quite well — there was a boundary. And I think she knew that marrying John Jr. would be stepping over that. And how do you deal with that? And I don't think anything can prepare you for the kind of onslaught that she had. A few friends compared her to Diana, that constant harassment from paparazzi. So it must've been a hard choice for her. And that's why she said, “I'll think about it.” I think she was really thinking about it, not just playing hard to get.

Your book illustrates how committed she was to neutral tones. I had read that she chose black because she wanted to be boring so the press would leave her alone. Is there truth to that?

There is and there isn't. This was one of the problems I had with the book — there is a lot of information out there that's never been properly verified. There were pictures that we just couldn't trace — this was the same with the rumors about Carolyn. I was very lucky to speak to a few of her very, very close friends — I'd say three of them were part of her inner circle — and the black clothes thing was the same as, “John Jr. made her dye her hair blonde.” One of them just went, “If [he told her to do that], she would've dyed her hair black.” She definitely had a thing about toning down her beauty — she wasn't always comfortable with the natural attention that she got before marrying John Jr. Maybe she did that by wearing black. I just never got any solid info to answer that question directly.

This is why the comparison to Diana or the British royals feels apt – there’s so much out there about them, yet what do we really know?

I think that that's the important part of their mystique. I think that's the part of Carolyn that we need to just revere and leave alone. She's kind of an open canvas for us to project what we want to project.

You have quotes from her throughout the book but they’re spare because she didn’t do a lot of interviews.

She didn't. And that was very deliberate on her part. I think she probably wasn't so comfortable with the press anyway, being a PR lady herself. I think John was the front man, he seemed to feel very at ease with them. You can see it in the very rare footage there is, she just lets him do talking. But when she does give her little quips, they're smart and they're witty. She's not without voice.

One of the most iconic images of her is from her wedding. What did you learn about her wedding dress?

She was definitely the instigator of what she wanted for the wedding. Basically, “I have this vision, this is how I want it to be.” I think she was ruminating about different ideas, and I think Narciso [Rodriguez, who designed the dress] was a natural choice for her. You have to remember that the wedding was very secretive, and not many people were meant to know about it. So what do you do when you're designing your dress? You can't go to Paris and get fittings because everyone's going to know.

This was the interesting thing about speaking to George [Kyriakos, her hair stylist]. He was very much part of that inner circle and said we were all friends just mucking in for our good friend who was marrying John Kennedy Jr. There was this rumor that she was taking her time and she was late to the wedding because she was being over-the-top or dramatic. But she'd lost quite a significant amount of weight from her last fitting, and Narciso was basically fixing that. There's this inclination to portray women as like diva-ish or difficult.

Loafers and a slip dress. Photo: Instar

Your photo research is extraordinary. How hard was it to track down all those pictures?

It was really painful. So many people have been like, But why didn't you include this picture? Some of the pictures we tried so hard to track down, but it was impossible. Things like Bill Cunningham's archives are not digitized yet. So many pap photographers are not alive anymore, and you need to find someone running the estate for them [to license the image] otherwise you could get into legal trouble.

This is also a curated book, an edit of all the pictures of Carolyn out there. Of course, there were issues with photo quality because nothing was digitized then. I kind of wanted to maintain that within the book, I didn't want it to be glossy and clean. There's a photo-album quality to it, and I think the layout presents it in a really beautiful way. I wanted it to be in keeping of the nineties — this is what photography was like at that time.

You know what makes the whole book feel cool is there’s may be, like, one photo of her on a red carpet.

Because they didn't have it in those times. They’re just walking into events. Robin Givhan actually wrote a brilliant article about the way that they held themselves, how they weren't spilling on this supposed red carpet about what they're wearing. And some of it still remains mystery to this day. Even though I sent boards to Yohji [Yamamoto] and Prada, and we were working through archives, there were still [looks] that they were like, we just can't say. And that was just extraordinary.

At a 1998 gala. Photo: Instar

How did you pick the cover image?

She had done three or four fashion shoots. That Bruce Weber shot was first done for Joe's Magazine, for Joe McKenna. Joe was close to Carolyn, and she agreed to do the shoot because the magazine was just for fashion insiders, a trade magazine. When she died, Susan White [the photography director] from Vanity Fair knew of this shoot and asked him, “Can we look at these pictures?” And it ended up being the bestselling cover of all time.

We reached out to Bruce. I just knew there wasn't any other one I wanted to do, and I wanted to do a shot that was different from the Vanity Fair issue. I just love this because a few friends spoke about how she used to speak with her hands, and you can actually see her hands coming out a little bit in the frame. Bruce [told me] she brought her dog, Friday, and she was just so at ease. She didn't wear any makeup. She just had painted toenails from an event the night before. She was just wearing a button down shirt. I feel like the paparazzi pictures are a little bit of Carolyn on edge, and this is just really her. And this is the woman that John Jr. fell in love with.

Get Carolyn Bessette Kennedy: A Life in Fashion. For more Carolyn, follow the book’s Instagram feed, and follow Sunita Kumar Nair here.