Timeless Princess Diana Outfits We Would Wear Today

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There was no denying that whatever Princess Diana donned turned into fashion gold.

The late Princess of Wales' eye for trends combined with a timeless aesthetic -- but not afraid to be daring from time to time -- made the royal an inimitable style icon. 2021 marks the 24th anniversary of her tragic death. To this day, we still look to Princess Diana for inspiration (just look at Rowing Blazers' Princess Diana collection). 

A true trendsetter, Prince William and Prince Harry's mother was ahead of her time, with pieces she wore decades ago making their way back into people's everyday wardrobe. We can still look back on her ensembles and confidently say, "I would totally wear that right now."

Ahead, ET Style is looking back on Princess Diana's enduring fashion moments. Plus, check out our selection of items to shop and channel the style icon. 


Long before Gigi Hadid and the Jenner-Kardashians sported bike shorts, Princess Diana was a fan of the athletic bottom. Leaving the Chelsea Harbor Club in 1995, the trendsetter wore a bright orange pair with a graphic sweatshirt, tube socks and sneakers. 

Princess Diana
Anwar Hussein / Contributor


Little Black Dress

Known as the "revenge dress" (worn on the night Prince Charles publicly confessed to having an affair), Diana turned heads in an off-the-shoulder black mini dress designed by Christina Stambolian, styled with a statement pearl choker necklace and pumps, for the 1994 Serpentine Gallery Summer Party. Single or taken, every woman needs a simply stunning black dress in the wardrobe. 

Princess Diana black revenge dress
Anwar Hussein/WireImage


Denim Outfit

A pair of high-wast jeans was a staple for Diana in the late '80s. She looked effortless and cool for an event at the Guards Polo Club in a graphic sweatshirt under an oversized blazer, styled with denim, slouchy boots and a trucker hat. 

princess diana at Guards Polo Club
Tim Graham/Contributor


Shop more Princess Diana-inspired items: 

With the continuing resurgence of '80s and '90s fashion, revisit more of Diana's best looks from stunning evening gowns to classic denim outfit formulas that are still incredibly chic, in the gallery below.

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