15 of Princess Diana’s most iconic fashion moments

Crummy weather shouldn’t keep you from looking your best. In her pre-wedding photos with Prince Charles, Diana wore green Hunter rain boots. The brand has seen a surge in popularity again in recent years, probably because they’re classic, timeless and durable.

 Princess look 

Diana wasn’t afraid to look like a girly girl, fully embracing her “princess” title. “At the beginning, her look was very ‘fairytale princess.’ There were lots of bows and frills,” Kerry Taylor, whose auction house auctioned ten of Diana’s dresses in 2013, has said. “She was the embodiment of every little girl’s fantasy of what it meant to be a princess.”

Bold patterns

Princess Diana didn’t shy away from bold outfits. She is seen here wearing a red and white polka dot patterned dress, a bright red blazer to match, and a white hat and red shoes. 

Pairing casual with polished 

Diana is known for her fancy dresses and gowns, but she could work a dressed-down look, too. She paired a collared white shirt with light wash jeans when on a trip to Bosnia in 1997.

Gold accents 

Beyond plain black tights 

Bring back old trends 

To visit her nation’s troops in 1995, Diana wore a pink skirt suit and pillbox hat à la Jackie O.

Floral dress 

Princess Diana looked gorgeous in this floral printed dress with a white blazer draped over her shoulders. Such a simple look is still in style today.