32 Gorgeous, Candid Photos of Carolyn Bessette-Kennedy

The late Carolyn Bessette-Kennedy, who became director of publicity for Calvin Klein before she met and married John F. Kennedy Jr., was a '90s fashion icon. In 1999, she and her husband tragically passed away in a plane crash. During her years as a public figure, Carolyn popularized a "throwaway-chic" style that was particularly emblematic of its time: minimalistic, unfussy, high-low (mixing expensive and inexpensive items), and personally expressive.

Carolyn was a very private person and refused offers to be featured in fashion magazines, although she increasingly appeared with her husband at various public events over the years. There was intense media coverage of her life and relationship—which Carolyn didn't enjoy or seek out—but it did endear an entire generation to her extremely chic style, which still has resonance today. We found 32 gorgeous, candid photos of Carolyn Bessette-Kennedy that contextualize her life—and looks—in new ways.

May 1999

This was John Jr. and Carolyn's last public event together. They're attending the John F. Kennedy Library Foundation dinner and Profiles in Courage awards (on the day of JFK's would-be 82nd birthday). Carolyn often wore black to events, and this structured skirt suit was a lovely matching moment with her husband.

March 1993

Pictured with Will Regan (her boyfriend at the time) at a Bloomingdale's event, Carolyn is in her element here: black beret, luxe leather jacket, simple but chic watch, and simple but classy jewelry. That, plus minimal makeup and natural hair worn down, is an encapsulation of how "effortless" her style was.

Circa 1994

According to the original caption, Carolyn and a model are on the phone "next to a statue of writer Gertrude Stein backstage at the RTW Calvin Klein spring/summer '94 collection." Her sweet grin is contagious; it's clear that the vibe isn't too serious.

May 1998

Here with Lee Radziwill (Jackie Kennedy's sister), Carolyn is at an afterparty for the Parsons Dance Company's premiere of composer Shelly Palmer's Anthem. Chic in black satin with her hair tied back in a simple updo, it's perfect for the event and also perfectly her.

April 1994

Here, perched on a stool next to stylist Polly Hamilton at the Calvin Klein Fashion Show in 1994, Carolyn is in the midst of work (still looking stylish, naturally, in a black jacket and matte lipstick). I also enjoy the emphatic no smoking sign in the back.

September 1996

This is such a "celebrities casually walking the streets of New York" photo: Carolyn, in all-black athleisure (way before it was cool) and contrasting white sneakers, and John Jr. in similar athletic gear and a backwards baseball cap. Carolyn wasn't a big fan of the media attention, and apparently she wore neutral colors to avoid attention from the cameras.

October 1996

Here, John Jr. and Carolyn look like any regular couple on a regular commute to work. John Jr. is casual in his trademark baseball cap and Carolyn is similarly low-key in her headband (both had the perfect balance of chill yet chic style); her wrap dress and boots are a classic 90s work look.

December 1998

While the lighting on this photo is a bit strange, this white column dress with full-length zipper is perfection on Carolyn. She's at the Universal Studios Fire & Ice Ball in Los Angeles, benefitting the Revlon/UCLA Women's Cancer Research Program. By now, she was doing more public events.

January 1997

A sweet (and vibrant) matching moment for Carolyn and John Jr., who are walking their dog in wintry New York weather. This is more vivid than we're used to seeing from Carolyn, and the black beanie and boots are a perfect example of how good she was with accessories.

May 1999

I really love this frothy, ruffled coat on Carolyn—it's so much more detailed and over-the-top than we usually see on her. The flare pants and nude heels are a nice counterbalance. Fun fact: This is one of only two times Carolyn ever gave a quote to the press (she never gave formal interviews, likely to combat the intense paparazzi interest in her).

Circa 1995

This super-casual photo of Carolyn and colleague Jenny Landy is a much more stylish version of two co-workers meeting outside. Apparently, Carolyn was recruited by a Calvin Klein exec, began working at their New York store, and rose to the rank of publicist and ultimately director of show productions when she left in 1996. She was considered a CK muse, according to Coveteur, and her style influenced the brand at the time.

March 1997

With some extremely '90s minimal shades and a simple tote bag, the accessories make the look here. Also, this is a great way to style a pair of flared khakis in such a way to look chic but still work-ready. It's no wonder this look is such an inspiration for "quiet luxury" enthusiasts.

January 1997

Carolyn's knee-high boots and tan skirt are a glimpse at a very smart work outfit underneath her belted black coat; her oversized camera bag and small briefcase add a dash of structure (and realism: this feels like a perfect commute outfit) to a simple ensemble.

October 1996

Standing in front of their Tribeca apartment, John Jr. and Carolyn face the photographers as a united front not long after the news broke that the two had gotten married (and had successfully kept it from the press). Carolyn is chic in a signature tan skirt (matching her blonde hair) and brown patent glove boots, with a v-neck sweater and small structured handbag.

October 1998

In a candid shot walking her dog (and inadvertently showing how persistent the paparazzi were in trying to get photos of her), Carolyn wears a tan coat, flared jeans, and black tote. While she sometimes changed things up, her look was overwhelmingly consistent—the sign of a person with a strong innate sense of style.

October 1996

This is probably the perfect example of Carolyn's high-low style: a simple black tank and crop flare jeans with strappy gold heels (such an upscale look to walk one's dog!). For context, this would not have been long after Carolyn left her job with Calvin Klein and had her secret wedding in September.

October 1997

After John Jr. and Carolyn got married, the media scrutiny on them only intensified. The two tried to continue about their daily lives; here, they walk around Tribeca after brunch at the restaurant Bubby's, according to the original caption. Carolyn's loafers and headband are perfection.

April 1996

At the Cartier presentation for the new Tank watch in Geneva, Switzerland, Carolyn and John Jr. listen intently. Carolyn's shoes and jacket are black, but her gorgeous golden dress, which matches her hair and skin tone, is a perfect example of how she elevated tonal dressing.

November 1996

Arriving at a reception at the Whitney Museum (one of a few times the couple would be photographed attending an event there), Carolyn pairs a low-cut dress with a simple black overcoat. After news broke of their marriage, the couple became an object of fascination.

March 1996

Carolyn and John Jr. leave their apartment on the way to an event. Carolyn almost always wore black to formal events, even when it was explicitly forbidden in the dress code (this, according to John Jr.'s old assistant RoseMarie Terenzio). Her heels are particularly glamorous.

September 1998

This is a closeup of Carolyn's gown at the Universal Studios Fire & Ice Ball in Los Angeles, with the long silver zipper bifurcating the dress. It was at this event that Carolyn gave one of only two brief interviews that were captured on video (we have almost no footage of her talking). Also, that red lip is spectacular.

October 1998

Here, attending the Municipal Art Society gala at Grand Central Terminal, Carolyn wears a sleeveless black column dress with matching long opera gloves and a thick bracelet worn over top. Even for the most formal of occasions, she still channeled her distinctive style.

May 1999

In a sweet, spontaneous moment, not long before both died in a plane crash in July, Carolyn and John Jr. embrace while attending the White House Correspondents dinner. The halter-necked dress is incredibly detailed and characteristically chic on Carolyn.

June 1996

In another sweet moment (not long before the pair would be married), John Jr. and Carolyn share a sweet moment at a Hilton Hotel event. Carolyn is, as usual, dressed in a simple black dress and slicked-back blonde hair with minimal makeup—she doesn't even have on any jewelry.

November 1997

At the second anniversary party of George Magazine, cofounded by John Jr., the couple walk hand in hand. Carolyn wears a deep lip shade alongside a signature black outfit; her hair's a little more tousled than usual, and she wears simple but high black pumps.

March 1999

These are probably the most famous public event photos of Carolyn. She and John Jr. are attending the “Brite Night Whitney” gala at the Whitney Museum of American Art; the combination of simple black skirt, simple Oxford shirt, and black sandals is so minimal but so perfect.

March 1999

In closeup, we get a more detailed look at Carolyn's gold bag, which basically stands in the place of bigger jewelry pieces (note that she has no jewelry on except for two small rings). You also see the daring cut of her shirt and how the impeccable fit of all her clothing was critical to her aesthetic.

April 1999 

In an oversized plaid blazer, Carolyn attends the Krizia fashion retrospective at the Grey Art Gallery (she was a lover of art and fashion her entire life). The cut is a little unusual for her, but she sticks to the classics underneath—a black slip dress.

July 1997

It's hard to see in close-up, but Carolyn wears a dark top and pants, as well as a cool rattan bag (not pictured). You can see her classic taste extended to sunglasses, too, and she looks particularly effervescent with minimal makeup and hair worn down as she walks on Madison Avenue.

April 1995

One of Carolyn's most exciting qualities was her magnetism. Here, she's at the Calvin Klein Collection’s Fall 1995 ready to wear runway show. She would have been dating John Jr. at this point (the two met at an event; then, he came to the New York office to try on clothes).

October 1992

Here, at the City of Hope party, long before she was Mrs. John F. Kennedy Jr., Carolyn wears a simple dress that suits her perfectly (whether it's Calvin Klein or not, it's definitely her aesthetic—and the brand's). It's a simpler time, and she looks happy.

Circa 1995

No big deal, just two cultural icons having a chat! This unexpected photo makes me smile, in part because it's a fun surprise that the two knew each other, but also because their looks are so similar. Great hair, black, sleeveless dresses, and cool factor for days.