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As a perpetual style icon of the 1990s, the preservation of Carolyn Bessette-Kennedy's fashion heritage was paramount. Upon early viewing, it's clear that Mance conducted thorough research, drawing from historical archives and private collections to dress the character of Carolyn. The series directly references numerous items that were uniquely part of Bessette-Kennedy's personal wardrobe. From the initial episodes, key elements of her distinctive style were immediately recognizable: minimalist separates for casual outings or her days at the Calvin Klein office, and sleek evening attire, consistently in black, for numerous social events. Each scene has been meticulously analyzed to identify the ready-to-wear pieces and accessories featured in the show, alongside their real-life inspirations.
In the narrative of "Love Story," Calvin Klein reportedly introduces Carolyn Bessette and John F. Kennedy Jr. at a 1992 benefit for the Amazon rainforest. While the historical accuracy of this initial meeting is debated, with some suggesting they first encountered each other at a Calvin Klein showroom during a suit fitting for Kennedy Jr. (a scenario explored later in the series), it is certain that Bessette-Kennedy favored elegant black dresses for evening wear. The particular dress selected for the series echoes a renowned strapless gown she wore to a gala at a later point. Although depicted without accessories in the show, one might draw inspiration from her typical embellishments—such as delicate pointed pumps, opera-length gloves, and a structured clutch—to emulate the aesthetic today.
Carolyn Bessette-Kennedy was the epitome of 1990s minimalist fashion, characterized by understated silhouettes, natural makeup, and effortless hair. Her office attire, as worn by Sarah Pidgeon in the series, appears to draw inspiration from a post-wedding ensemble Bessette-Kennedy herself wore in New York City. This look features a black V-neck sweater, a camel pencil skirt, and brown leather knee-high boots—timeless, neutral pieces that remain stylish today. Her accessories were always simple, including a structured tote and often a tortoise headband from C.O. Bigelow, paired with a subtle gold ring.
The early scenes of "Love Story" showcase Bessette-Kennedy's quintessential style, offering glimpses into her evolving fashion throughout the series. A notable early depiction shows Pidgeon's character en route to meet John F. Kennedy Jr. at what is presumed to be the East Hampton airport, sporting a classic Bessette-Kennedy combination: a black top paired with brown trousers and oval sunglasses (hers were by Selima Optique). This pairing was a consistent feature in her casual wardrobe, whether it involved a simple black cardigan and khaki pants or an oversized black button-down with brown trousers. She often complemented these relaxed outfits with leather loafers for comfortable travel, and for a contemporary interpretation, a similar straw bag could be added for transitional spring styling, a choice also favored by modern icons like Zoë Kravitz.
For a chance encounter at Kelly Klein's "Pools" book launch party, the character portrayed by Pidgeon is dressed in a refined black slip dress with a high neckline—a signature piece that Bessette-Kennedy frequently relied on for formal occasions. Black tailored coats were also a staple in her closet; to replicate this look, layering one over the dress would be essential. The ensemble is completed with sleek pointed pumps and a touch of color on the lips—despite her preference for minimal makeup, Bobbi Brown's Ruby lipstick was a characteristic shade she wore for evening events. While perhaps looking ahead, incorporating a sapphire and diamond eternity engagement band into the concept adds a timeless touch of jewelry to any evening attire.
