The first image of Carolyn Bessette-Kennedy that truly stayed with me was disarmingly simple: a black coat, hair slightly tousled, Selima Optique sunglasses, Levi’s bootcut jeans, and a pair of bright yellow loafers. It was the shoes that stopped me. She was wearing python yellow loafers from a mid-1990s Prada collection—an incredibly rare style that I would think about for years.
Color was never central to Bessette-Kennedy’s wardrobe, especially not after her relationship with John F. Kennedy Jr. brought heightened visibility, yet here it appeared, on her feet. I loved that restraint. The unusual yellow hue and python texture felt almost private, a way of asserting personality without disrupting the quiet uniform she became known for. In a decade increasingly defined by minimalism—both in color and silhouette—that single detail revealed to me how thoughtfully she approached self-expression: The discipline in her wardrobe was intentional, but not limiting.
Those shoes eventually inspired me to source an entire collection of her most iconic footwear, a process that took over a year of meticulous secondhand sourcing. While the exact python loafer continues to elude me, I was able to find the Mary Jane version from the same collection, along with several other pieces she wore repeatedly: her beige Mary Jane Manolos, patent leather Prada loafers, and her beloved Spazzolato tote.
Carolyn Bessette-Kennedy’s Key Wardrobe Essentials
As ’90s nostalgia continues to grow, pieces from Bessette‑Kennedy’s closet are notoriously difficult to find; they require meticulous knowledge of the exact year, designers, colors (although perhaps the lack of colors she wore makes tracking down her pieces even more difficult), and the exact styles she wore.
Of course, she had her favorite designers such as Prada, Yohji Yamamoto, and Manolo Blahnik, but even the items she wore (and often rewore) are increasingly hard to spot on the vintage market. For those who are looking to source her exact pieces, I always suggest studying her street style photos—you’d be surprised by the nuance and precision of her choices. And while her wardrobe can’t quite be replicated the way a certain celebrity look might be today, it’s her approach to style that’s become a lasting point of reference; one that continues to inspire people to dress like her—myself included.
Decoding her outfits means looking beyond labels and focusing on the elements that made her style timeless: impeccable cut, repetition, and confidence in simplicity. As a vintage curator, I’m constantly framing my references around her. My own style, minimalist in nature, is centered around an ethos she practiced daily: choosing pieces with care and intention, to stand the test of time.
When you consider the evolution of her style—from before her marriage to after—you can see how deliberate she was in her curation. Her clothes became more monotone in color, with fewer patterns, but remained rich texturally. While we know that Bessette‑Kennedy never aimed to be the style icon she’s revered as today—she often dressed in a way to avoid unwanted attention—her outfits were made up of enduring pieces that now form the building blocks of many “minimalist capsules.”
After years spent decoding her wardrobe and sourcing pieces she wore, I was able to contribute a few vintage pieces for Ryan Murphy’s upcoming show, Love Story. In revisiting her decade-defining style, certain looks continue to rise to the surface, not for their drama, but for their discipline and uniqueness. These are the looks I hope to see echoed, charting her evolution of self-expression, from her more laidback moments to the poised uniform that would come to define her.
Bessette-Kennedy mastered evening elegance while still staying true to her style. Here she’s wearing one of her favorite Manolo Blahniks—patent black leather Callasli’s—which she used to shop herself at their store on West 54th street. Manolos were a constant in her wardrobe—the brand was her go-to for countless appearances and, most notably, the shoe of choice on her wedding day. Though the evening’s dress code was “bright and beautiful,” Bessette-Kennedy stuck to a tried-and-true neutral color palette, pairing a crisp white shirt with a black ruffled skirt by Yohji Yamamoto, adding a hint of glimmer with a Whiting and Davis mesh gold purse. It’s one of her most referenced looks to this day.
One of the rarer images of Bessette-Kennedy embracing color, here she is captured on a walk with JFK Jr. and their dog, Friday. Carolyn is wearing a vermillion red checked Prada coat, paired with her signature bootcut jeans and square-toed Prada boots—two silhouettes and a brand she loyally wore.
Bessette-Kennedy’s love of loafers and pants is well-known, captured here in a quintessential off-duty look while walking back to her Tribeca apartment. She paired her toffee-colored cords with a slim-fit black turtleneck and classic Manolo Blahnik loafers, Selima Optique brown sunglasses, and a lived-in Hermès Birkin—a combination that feels as relevant now as it did then. Bessette-Kennedy favored practical shoes for moving through her neighborhood (walking the dog, running errands), reserving heels for galas and other more formal occasions. Throughout her relationship, Bessette-Kennedy maintained a desire to move independently and comfortably through the city, dressing for real life rather than spectacle, which is arguably why she continues to inspire so many today.
Captured mid-stride, here she walks her dog, Friday, in pared-back yet perfectly fitting essentials she returned to often: Levi’s bootcut jeans, a sleeveless black top, her Cartier Tank Louis, and Prada sandals that are extremely rare to find today—a low-key uniform that defined her approach to off-duty dressing.
While it was rare to see Bessette-Kennedy in a floral, this 1996 Chanel dress is one that is reminiscent of her more playful style. On a warm summer day, she paired the knee-length, cap-sleeve dress with two of her most well-worn Prada pieces: a pair of black slingback heels and her patent 1995 Spazzolato bag.
Here’s another example of Bessette-Kennedy’s everyday uniform, formulated around hardworking basics: a structured black Prada coat, heeled Prada boots, bootcut jeans, and her fail-safe 1995 Prada Spazzolato bag.
A perfect example of Bessette-Kennedy’s considered yet unfussy approach to evening wear: a form-fitting black dress, satin Manolo Blahnik heels, elbow-length gloves, and minimal makeup for an art gala in 1998. While this was worn almost 30 years ago, this outfit has stood the test of time and is proof that simplicity, when done with intent, never dates.
One of Bessette-Kennedy’s most recognizable off-duty looks—simple in construction, but elevated by accessories that have endured. Her Selima Optique sunglasses, a Charles Wahba headband purchased from C.O. Bigelow, and a Prada wallet were defining elements of her wardrobe, proving how singular details could anchor an entire look. She paired her signature accessories with two other staples: bootcut Levi’s and black Prada boots.
A more serious moment, captured shortly after their engagement, when JFK Jr. publicly asked for privacy for his new wife. Bessette-Kennedy appears composed and restrained, dressed in a black sweater paired with a beige Prada skirt, brown patent leather Prada boots, and her black Spazzolato Prada bag. The look reflects the quiet discipline that would come to define her later style: refined and intentionally understated.
Lastly, here’s an image of Bessette-Kennedy in a relaxed, off-duty look from when she was still working as a fashion executive at Calvin Klein, during the earlier period of her relationship with JFK Jr. She’s wearing a red parka layered over black sweatpants and sneakers—a reminder that even then, her everyday uniform leaned practical and unfussy, grounded in function rather than flash. It’s an outfit that feels strikingly familiar today, something you might wear on a quiet Sunday, walking around the neighborhood.
