For her September 21, 1996, wedding to John F. Kennedy Jr., Carolyn Bessette was ready to surprise. It was one of the most anticipated nuptials since Princess Diana and Prince Charles, but instead of a cathedral filled with thousands of people, the couple chose the First African Baptist Church on Cumberland Island, Georgia, with about 40 guests in attendance. For their rehearsal dinner and reception, they celebrated at the island’s Greyfield Inn, where most of their guests stayed as well.
The wedding was an event, but the dress was what changed everything. Bessette chose her close friend Narciso Rodriguez, who had worked with her at Calvin Klein, and instantly made the designer a household name; the next year, he launched his own eponymous label. “It was a great moment in my career but also a beautiful moment in my personal life,” he told Vogue in 2018. “Someone I loved very much asked me to make the most important dress of her life.” That life turned out to be much shorter than anyone expected at the time—Bessette-Kennedy was 33 when she and her husband died in a private plane crash in July 1999.
Her fashion legacy, however, lives on. Twenty-five years after Carolyn Bessette-Kennedy “hands down changed the wedding dress game,” the people who watched it happen look back.
The most famous photograph of the evening was captured by Denis Reggie, a longtime Kennedy family photographer who says he has captured 25 Kennedy weddings. He snapped the newlyweds as they descended the steps of the candlelit church, which had no air-conditioning and only eight pews.
Reggie: It was an incredibly magical moment. I saw it as it was unfolding, almost in silhouette. It was virtually dark outside. John reached for the hand of Carolyn; she was caught off guard. I’m walking backwards in the light rain at dusk, and John does this amazing gesture, taking her hand and bringing it to his lips.
John and Carolyn asked Reggie to choose the photo that would be released to the public two days later, on Monday, September 23.
Reggie: It was lovely, the spontaneity of that gesture. For a celebrity to be that warmhearted and showing his love in that way—it was great. The previous time we’d seen John Kennedy with an expressive gesture was 33 years before, at the burial of his father on his third birthday. It was such a telling, interesting moment, him saluting his dad. Then, at his own wedding, another incredibly kind, princely gesture. I was really moved by it and Carolyn’s surprise. I adored her expression—it says it all. The way she flowed in her beautiful dress, moving at full pace, coming down the steps. It was happening in real time, and not in any way posed or arranged. It was indicative of the way the wedding was—natural and of the moment, not trying to be any more than it was in its simplicity. It had such an incredible elegance and romance; the authenticity of it all, its simplicity gives it real power. It was a really special photograph.
What I remember most was the way they were around each other. They exuded an affection that was beautiful to witness, the love felt that weekend and that night on Cumberland Island. That’s what I remember most—the magic feeling of the two of them together, the way they were.
Carolyn’s veil was made of silk tulle, and she wore crystal-beaded satin sandals from Manolo Blahnik; on her arms were long white gloves, and in her hands were an understated bouquet of lilies of the valley. Her hair was pinned into a bun and held by a clip that once belonged to her mother-in-law, Jacqueline Kennedy Onassis. She specifically asked that the photo Reggie chose to release show off Rodriguez’s dress.
Reggie: She said, “Show the dress. My dear friend designed the dress.” She knew it would be a moment where the dress would show fully…. The dress was lovely, and very fitting. She certainly wore it beautifully and it was made for her. It was lovely in its simplicity and elegance and was very much consistent with the theme or feel of the wedding. It was five-star perfection.
Former Harper’s Bazaar editor in chief Kate Betts, who at the time was working at Vogue: We were a generation that grew up watching Diana get married on TV in 1981 in that iconic wedding dress. In 1996, it was still a pretty iconic wedding dress. Vera Wang and Carolina Herrera were simplifying their designs, but not as simple as a slip dress. [Carolyn’s dress] was revolutionary in that sense, that someone would wear something that simple. It crystallized that trend [minimalism] in fashion. That was her aesthetic, and her wedding dress was a very, very bold expression of that minimalism.
Fashion designer Ann Mashburn: [Carolyn] worked in fashion and was a fashion person. Having worked for Calvin Klein, her dress made sense to me. She dressed like that in photos and when I saw her in the Calvin Klein showroom. To have it be a slip dress is a bold thing to wear; it’s not even corseted. You have to be confident; I could never wear it. Her dress was perfect for where she got married.
Actress and author Jill Kargman: When you think of other huge, iconic wedding dresses prior, you think of Princess Diana. This dress was totally opposite and diametrically opposed. Both are iconic in different ways. She did her own thing. I definitely feel like it broke the mold of the moment.
Fashion designer Cynthia Rowley: I was so awestruck at the time with its simplicity. It’s so sleek and sexy at the same time, so glamorous. It has the same sort of simplicity and sex appeal, kind of a boudoir feeling, of when Marilyn Monroe sang “Happy Birthday, Mr. President.” It kind of has the same “dropped onto the body” [feel]. [At the time] nothing was as stripped down to that level of lingerie, basically.
Fashion journalist Zanna Roberts Rassi: It was the epitome of ’90s minimalism. I remember how cool and bold it was, breaking all bridal rules in the most elegant way possible. Only a woman with a real sense of self can do that. It was a bold move in an era of froufrou; she brought this kind of palette cleanser, a sort of refreshing sorbet after a fancy meal.
Style expert Stacy London met Carolyn many times on the fashion circuit. “I’ve never met somebody so arresting,” London says. “I was just absolutely amazed by her. She was the epitome of chic.”
London: [The dress] has the most extraordinary construction—simple, bias-cut, all of it. [The dress] emphasized and highlighted the woman wearing it. What I saw was [that] Carolyn’s dress was a vehicle to shine light on her…. This was really a statement about the dawning of a new age, very much in keeping with Narciso’s entire aesthetic, the idea that true simplicity can be absolutely, exquisitely beautiful.
What struck me about the dress is it was so bare—no ornamentation, no rhinestones or sequins or even embroidery. She was just one of those women who understood how to make fashion work for her, not the other way around. She just was who she was, and part of her appeal came from not trying to be anything other than herself. She understood how to not have the clothes be the focus—she was always the focus. She understood that an understatement was the loudest statement in the room.
Betts: Nobody knew they were getting married, then that was a shocking part of the whole event—she was wearing this very simple dress at a very simple, secret wedding. This look was an expression of her personality, that she’d do things on her own terms, in her own style, with her own point of view.
People are still dressing in that kind of design for their weddings, and people are definitely still inspired by the dress in many different ways. Its simplicity really changed the whole nature of the bridal industry—that whole idea of wearing a much simpler wedding gown has become a classic bridal expression now.
Meghan, the Duchess of Sussex, has openly shared her admiration of Carolyn’s style. In an interview with Glamour in early 2016, the then Meghan Markle, when asked which celebrity wedding dress was her favorite, named Carolyn’s, calling her gown “everything goals.” Even nearly two decades after her death in 1999, Carolyn’s impact on fashion and culture remains: Fashion designer Wes Gordon modeled one of his collections after Carolyn in 2016, and Rosamund Pike partly modeled her character in the movie Gone Girl after Carolyn.
Mashburn: It is a timeless dress. Whatever she wore for that wedding would have been memorable. The flowers she carried, everything about it was very casual in a time when bouquets didn’t really look like that.
Kargman: The spotlight that A-listers have to endure—the dress was a chess move away from that. It wasn’t like “Oh, I’m marrying into Camelot with a 20-foot train.” It was a complete chess move in the opposite direction. I feel like more people should be like that—understated, not over the top, [not] attention seeking. I really respect that. With the fame fuckers now, it’s so refreshing she chose to turn the spotlight down rather than up.
Rowley: I definitely think it does feel like that kind of simplicity will never go out of style. It never shows its age. It proves that, while experimentation and trends are fun and entertaining in fashion and are exciting and stimulating, I think in some cases the simplicity of something so clean and light and classic sometimes actually has more impact than some crazy over-the-top thing. I think the quietness of her dress is proving that can almost have more impact than anything else. When everything else is pared down, you see the person for who they are and see their beauty. Her beauty is this pure, classic beauty; instead of seeing her as this fashion object, we’re really looking at her.
Roberts Rassi: It has held up more than most dresses; it’s perhaps better today than it was then. How many dresses can we say get better and better? It has had a massive cultural impact, particularly with the new generation. It’s so interesting to see how the next generation is completely obsessed with her. She’s a woman of mystery, something we don’t have much of today. That’s part of the magic—less is more. We’re left wanting so much more. That’s definitely part of the appeal.
London: I honestly can’t believe 25 years have passed. I think that kind of dress will now forever be the moment we realized being a bride doesn’t mean you have to look like a fairy princess. You don’t need a ball gown with bells and whistles. Something about that dress transcends trends and time—almost no bridal establishment would say they don’t have at least one dress that resembles it. It has become a cultural touchstone.
[The dress] was nothing we had considered or seen before, but Carolyn and Narciso knew it was right for her. Not for everybody—but for her.
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