Recreate Carolyn Bessette Kennedy’s Iconic Look with Vintage Finds

Before Phoebe Philo stepped into her role at Céline, before the Olsen Twins and The Row dominated quiet luxury, there was Carolyn Bessette Kennedy.

Carolyn remains one of the most enduring style icons of the late twentieth century. Known for her quiet elegance, she captured public fascination with her iconic street style and continues to influence fashion decades after her untimely passing.

In early 2026, the Ryan Murphy-produced television series, Love Story: John F. Kennedy Jr. & Carolyn Bessette, starring Sarah Pidgeon as Carolyn, debuted to critical acclaim, thanks in part to the near-perfect styling of the titular ‘It Girl’, introducing a new generation to the style icon.

Considering Carolyn was one of the most photographed individuals of the 1990s, the pressure was on to ensure Pidgeon’s styling looked the part. Thanks to Love Story’s costume department sourcing vintage pieces from Carolyn’s favorite NYC vintage store, What Goes Around Comes Around (WGACA), the show's styling looks like it stepped right out of 1996.

With help from WGACA, the pitch-perfect soundtrack pulled straight out of the ‘90s, and awards-ready acting from the ensemble of talented performers, Love Story has gone viral across all social media platforms. TikTok videos of couples dressing up as Carolyn and JFK Jr., Instagram posts discussing Carolyn’s street style, Pinterest boards of deconstructing the outfits on the show for mainstream consumption, all culminating in the creation of one of the season’s most talked-about pieces of media.

2026 is shaping up to be the year of Carolyn Bessette Kennedy street style, and you can make that 2026 aesthetic a reality with the help of WGACA and shopping vintage.

From Fashion It Girl to American Royalty

Carolyn Jeanne Bessette was born on January 7, 1966, in White Plains, New York, and grew up in Greenwich, Connecticut. Her career took shape at Calvin Klein in New York City, where she eventually became a publicist and developed close relationships with high-profile clients and members of the fashion industry. It was during this time that she became known within fashion circles for her striking presence and naturally refined sense of style.

Carolyn’s life changed dramatically when she met John F. Kennedy Jr., the son of John F. Kennedy and Jacqueline Kennedy Onassis. Their relationship drew significant media attention and after several years of dating, the couple married in a private ceremony on September 21, 1996. The wedding itself became a cultural moment, particularly because of Carolyn’s understated gown designed by Narciso Rodriguez, which perfectly embodied the restrained elegance that defined her style.

Her accessories played a major role in shaping her image. Among the most recognizable were her Hermès Birkin 40, Prada bags, vintage slip dresses and tortoiseshell headbands. At a time when many luxury houses emphasized logomania and monograms, bags from Prada and Hermès (like her well-worn Birkin 40 and Prada Spazzolato tote) mirrored Carolyn’s preference for subtle sophistication, reinforcing the idea that luxury could be quiet rather than loud.

Carolyn wore her luxury pieces. Like, actually wore them. She carried her Birkin on the subway, packed it to the brim and was rarely seen without a bag on her arm.

One of the most enduring quotes about Carolyn came from JFK Jr.’s assistant RoseMarie Terenzio, who said to Vogue: “She didn’t have 75 handbags. The Prada bag was her everyday bag for a year.”

Another signature element of her wardrobe was denim, particularly Levi’s jeans. Carolyn often wore classic Levi’s 517 bootcut jeans, paired with simple black sweaters, crisp white shirts and long wool coats. The pairing of heritage American denim with luxury accessories created a look that felt authentic and balanced. Her Levi’s became symbolic of the relaxed yet polished aesthetic that many continue to emulate today.

The New York Post: In Conversation with WGACA CEO Seth Weisser

On March 7th, 2026, The New York Post released an article on Carolyn Bessette Kennedy’s favorite NYC vintage shop in conversation with Seth Weisser, CEO of WGACA. WGACA’s West Broadway Flagship location was a less than ten-minute walk from Carolyn and John’s Tribeca loft, so it was kismet that she would venture into the store in the ‘90s to shop for the best vintage New York City had to offer.

When asked about Carolyn, Seth said: “She was just so very polite and so sweet. She bought a lot of Levi’s from us because Levi’s was the go-to for every ‘It Girl’ and still is. She was early in that appreciation of what that was.”

Along with her favorite style of denim, Levi’s 517, Carolyn would purchase evening gowns to wear to events with John.

It made sense that the costume department of Love Story would come to the source of New York City’s best vintage fashion and Carolyn’s favorite place to shop to source pieces to style actress Sarah Pidgeon. The team purchased multiple vintage pieces from WGACA, and these pieces can be seen on Pidgeon in multiple scenes of the show.

Seth’s final thoughts on CBK were heartfelt and appreciative: “Through word of mouth was how our business grew so organically. So, through her friends and her social circles, because she was wearing cool pieces, she told people about us, and it was part of how we’ve grown to last as long as we have.”

Want to Dress like CBK? Try These Iconic Pre-Loved Pieces from WGACA