The Tamesis
The first image of Caroline Bassett-Kennedy that really struck me was reassuringly simple: a black coat, slightly tousled hair, Selima Optique sunglasses, Levi’s bootcut jeans and a pair of bright yellow loafers. It was the shoes that stopped me. She wore python-skin yellow loafers from the mid-1990s Prada collection—an extremely rare style that I’ve been thinking about for years.
Color has never been central to Bessette Kennedy’s wardrobe, especially after her relationship with John F. Kennedy Jr. brought greater visibility, but here, it’s on her feet. I like this restraint. The unusual yellow hue and python texture felt almost intimate, a way to make a statement without disrupting the quiet uniform she’s known for. In a decade increasingly defined by minimalism (both in color and silhouette), this single detail revealed to me how thoughtful she was about self-expression: the rules of her wardrobe were intentional, but not restrictive.
These shoes eventually inspired me to source an entire collection of her most iconic shoes, a process that took over a year of meticulous second-hand sourcing. While the exact python loafers still baffle me, I tracked down a Mary Jane version from the same collection, along with several other pieces she wore over and over again: her beige Mary Jane Manolos, patent leather Prada loafers, and her beloved Spazzolato handbag.
Caroline Bassett-Kennedy’s Wardrobe Essentials
Citizen Caradene turtleneck sweater
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Polo Ralph Lauren loose fit button-down shirt
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As ’90s nostalgia continues to surge, pieces from Bessette-Kennedy’s wardrobe are becoming increasingly difficult to find; they require meticulous knowledge of the exact year, designer, color (although tracking her pieces may be more difficult due to the lack of colors she wore), and the exact styles she wore.
Sure, she has her favorite designers, like Prada, Yohji Yamamoto and Manolo Blahnik, but even pieces she’s worn (and often re-worn) are increasingly difficult to find on the vintage market. For those looking to find her exact work, I always recommend studying her street style photos – you’ll be surprised by the nuance and precision of her selections. While her outfits can’t exactly replicate what a celebrity is wearing today, her fashion style has become an enduring reference point; she continues to inspire people to dress like her—myself included.
Interpreting her clothes means looking beyond labels and focusing on the elements that make her style timeless: impeccable tailoring, repetition and a confidence in simplicity. As a vintage curator, I constantly use her as a reference. My own style is minimalist in nature, centered around the ethos she practices every day: carefully selected pieces that will stand the test of time.
