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Jackie O x Princess Diana

August 19, 2022
By Jillian Dembs

Jackie O and Princess Diana are two first ladies with celebrated style globally. During their reigns, these figures maximized their public influence, making the case for era-specific style that ignited their audience's inner-fashionista.


Jackie O became First Lady in 1960. Experimenting with style popularized in this decade, as the USA drew closer to the expressional freedom in the 70s. Jackie O, in particular, was remembered for her lady-like elegance, embodied in every classy, polished silhouette she sported. Women across the nation admired her as a style mogul because of her effortless poise in the media. Jackie universalized many a trend from pillbox hats to Chanel suits to oversized round sunglasses. She fused elements of masculine with elegant and effeminate pieces that surprised and impressed women worldwide. Rocking a pair of pants (even denim!) inspired women to resist the conventional boundaries of womenswear.


Princess Diana officially received her royal title in 1981. As we all know, fashion during the 80s was lawless. As a new Princess in the media, Diana boasted her quirky style with polish, just like Jackie O. Diana also explored the casual “off duty look;” her biker-short x crewneck combo was her claim to fame. Diana’s approach to dress felt more relatable to the public because of her fairly traditional upbringing. She transitioned into the royal palace, embodying the essence of a Princess, while maintaining her true charm.

Now, let's break down a few looks from each that really capture what it means to be a first lady fashion icon.

One of Jackie O’s most famous looks was from a White House event in 1962 where she wore a pink Christian Dior strapless gown. Paired with white gloves, a clutch, and heels, the silhouette revealed Jackie’s elegance and grace. Just two years into being First Lady, Jackie was already embracing a luxurious taste, and of course, what it meant to be “lady-like.” 

Princess Diana, at an opening for the Victoria and Albert Museum, wore a custom blue strapless gown by Beville Sassoon, paired to a glamorous diamond choker, clutch, and heels. This was her first year as Princess and the world’s eyes were all on her. The choice of evening wear illustrated her elegance, class, and decadent taste at such an early stage of royalty. Both Jackie and Diana champion sophistication and charm with their own voice, making them exemplary fashion figures for years to come.