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-1990’s 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 second-hand 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 re-wore), 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.