Princess Diana wasn’t just a royal – she was fashion’s original disruptor. She played by her own rules, knew the power of a headline-grabbing outfit, and basically gave the 1980s and ’90s their most unforgettable style moments. Here are 10 of her most iconic looks – ranked, remembered, and still very much on our mood boards.
1. The Black Ball Gown (1981)
Embed from Getty ImagesBefore she was Princess Diana, she was just shy Di – then she showed up in a strapless black gown and instantly shut that down. Ruffled, plunging, and royally rebellious, this was her fashion mic drop.
2. The Fairytale Wedding Dress (1981)
Embed from Getty Images25-foot train. 153-yard veil. 10,000 pearls. Diana’s wedding gown was basically the Pinterest wedding board before Pinterest existed. The puff sleeves and huge glam? Peak ‘80s bridal – and totally unforgettable.
3. The OG Statement Sweater (1981)
Embed from Getty ImagesA red knit jumper with one black sheep among white ones? Diana wore it twice. Whether she meant it as royal shade or just loved the vibe, it became iconic. In 2023, it sold for $1.1M.
4. The Velvet Gown (1985)
Embed from Getty ImagesShe danced with John Travolta at the White House in a midnight-blue velvet gown that hit front pages around the world. It was old-school Hollywood meets royal glam -instantly iconic and still referenced in fashion history today.
5. Di in Sequins (1986)
Embed from Getty ImagesThis sea-green Catherine Walker gown delivered peak ‘80s glam – strong shoulders, full sequins, and all eyes on Diana during her state visit to Vienna. Power dressing at its finest, polished, confident, and unforgettable.
6. Cannes Film Festival (1987)
Embed from Getty ImagesDiana floated into Cannes in an ice-blue strapless gown and matching chiffon scarf. Inspired by Grace Kelly and the Riviera breeze, it was one part movie star, one part real-life princess. Grace would’ve approved.
7. The “Elvis” Dress (1989)
Embed from Getty ImagesWhite, covered in pearls, and finished with a sharp collar, this look was peak late-’80s flash. Diana called it the Elvis dress – perfect for an era of MTV, fashion awards, red carpets, and nonstop photo ops.
8. The ”Revenge” Dress (1994)
Embed from Getty ImagesPrince Charles confessed to cheating. Diana didn’t say a word – she showed up in a black off-the-shoulder mini dress with a chiffon train. It was pure 90s tabloid gold, and the timing couldn’t have hit harder.
9. Biker Shorts and a Sweatshirt (1995)
Embed from Getty ImagesBefore model off-duty was a thing, Diana was doing it in Virgin Atlantic merch and bike shorts. She wore the same gym look repeatedly to troll paparazzi – and accidentally invented today’s go-to casual fit.
10. Met Gala (1996)
Embed from Getty ImagesA navy silk slip dress with lace trim by Dior? Chic. A sheer chiffon robe draped on top? Regal. This was Diana in her post-divorce era – confident, elegant, and redefining red carpet rules on her own terms.
Diana’s style still sets the bar – decades later, we’re all still drawing inspo from her best looks. From dramatic gowns to off-duty cool, she nailed every vibe. Tag us in your favorite Diana-inspired fits and follow for more iconic style inspo on the daily. ✨
SEE ALSO:
- Best Looks from Carrie Bradshaw – TV’s Ultimate Fashion Icon
- Who Dressed the Best at Glastonbury Festival? Let’s Break It Down
- The Most Iconic Celebrity Wedding Dresses of All Time
