After keeping their engagement hidden from the press, the pair confirmed their union on an island off the coast of Georgia with only 60 guests. Kennedy wore a navy suit with a sky blue tie, while Bessette-Kennedy opted for an ivory Calvin Klein silk slip dress with Manolo Blahnik pumps. To contemporary eyes, the dress is merely an elegant piece, but in the ’90s, it made a distinctive statement in the sea of ornamented and voluminous gowns (see Princess Diana’s dress) which dominated the era. The decision worked in Bessette-Kennedy’s favor, allowing her sky blue eyes, blonde hair, and red lips to stand out in all their glory.
Though Bessette-Kennedy is no longer with us (herself and JFK Jr. died in a plane crash in 1999), her polished sense of style lives on. Through the minimalist collections of The Row and Tôteme, we get to imagine how the fashion maverick would have worn these contemporary brands and their product offerings (we bet she would have been an early fan of the former’s Ginza Leather Thong Sandals). Instead of just hypothesizing, though, why not take a look at some of Carolyn Bessette-Kennedy’s style moments for yourself?
From what to wear to a fall gala to a New York City spring day, below find your fashion blueprint for all fashionable events.