Before the days of Instagram, TikTok or blogs critiquing royal fashion, it was up to the media to track what royals like Princess Diana were wearing. While she was often applauded for her elegant Catherine Walker coat dresses and sleek Versace evening gowns, Diana’s casual looks didn’t always sit well with the press. In Dianaworld: An Obsession, author Edward White explores the world’s fascination with the late royal, including how her laid-back ’90s wardrobe fell short to a public expecting tiaras and elegance.
The author writes that when Princess Diana visited the island of Nevis in 1993, members of her hotel staff “reported disappointment” about her outfits. Quoting journalist James Whitaker, White adds, “the woman who arrived in the dining room for dinner each evening was not dressed to the nines. ‘Why can’t she wear some diamonds?’ one employee asked.”
Calling “being seen in public in jeans” and a tee as “acts of crossdressing” for Diana, White continues that her casual wardrobe in the mid-’90s “caused consternation.” Many fans “looked to Diana and her wardrobe to project what Catherine Walker’s designs hinted at: a notion of magical Englishness,” he adds. Several U.K. publications picked apart her denim outfits, with White writing that Diana “was ridiculed” by Tatler for “wearing white jeans and chunky gold jewelry.”
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Princess Diana went for classic mom jeans with Prince William in 1992.
(Image credit: Getty Images)
She rocked a Canadian tuxedo in Lech, Austria, in 1993.
(Image credit: Getty Images)
While Diana always wore casual outfits from time to time, she began to lean into a more American style featuring jeans, T-shirts and ball caps after her separation from Prince Charles in 1992. In one famous 1994 photo she even wears a Philadelphia Eagles varsity jacket, a gift she often sported in the years before her death.
She still wore smart suits and evening gowns when official occasions called, but her more relaxed wardrobe reflected Diana’s new life outside of palace restrictions. That being said, writer Anne de Courcy went on a tirade in the Daily Mail about the “Sharonisation of Diana,” with White explaining, “Sharon being a name that came to be associated with the aspiring working-class population of Essex in the 1990s.”
Another Daily Mail story about the princess referenced popular British shows at the time, proclaiming, “Will the real Diana please sit down, turn off Birds of a Feather, forget the Queen Vic [the pub in East Enders] and dress like a princess.” One paparazzo took it a step further, telling Diana in the mid-1990s, “put your head up and start acting like a fucking princess.”
The late royal couldn’t get enough of bike shorts and crewneck sweatshirts.
(Image credit: Getty Images)
The Lady Di Look Book: What Diana Was Trying to Tell Us Through Her Clothes
Undeterred, the late royal continued to wear her favorite pieces—Virgin Atlantic sweatshirt and bike shorts included—despite their “supposed vulgarity,” as White writes.
Eloise Moran, author of The Lady Di Look Book, notes Princess Diana’s workout outfits were somewhat of a revolution. “It was simply unheard of at the time for any British princess to be caught in workout gear other than the usual equestrian togs, not to mention in Polo Ralph Lauren sweatshirts emblazoned with giant ‘USA’ logos,” she writes.
Whether it was one of her Harvard crewnecks or her bright white shorts, Diana “purposefully recycled her gym outfits over and over, in the hopes that the press couldn’t get any new photographs of her,” Moran adds.
