News Princess Diana Wore Her Best Outfits on Halloween Fashion over festive. By Christopher Luu Christopher Luu Instagram Twitter Christopher is a Southern California-based editor and has been with InStyle since 2018. He covers all things entertainment, celebrity, and culture. InStyle's editorial guidelines Updated on October 15, 2019 @ 07:45PM Pin Share Tweet Email Halloween may be more about getting into character than attending balls, but when you're the Princess of Wales, scheduling conflicts mean that the bride of Frankenstein getups stay in the closet and floor-sweeping gowns come out to play. Princess Diana happened to have a few iconic fashion moments on All Hallows' Eve. No, they're not as eye-catching as some other celebrity Halloween costumes (or as controversial), but they stand the test of time a little better than something from Stranger Things. Anwar Hussein/Getty Images Richard Gere and Sylvester Stallone Nearly Got Into a Fist Fight Over Princess Diana At a ball in 1985, when Prince Charles and Diana were in the midst of a royal tour of Australia, the two went to a ball held on Halloween. Diana's outfit included a jeweled headpiece and a very '80s dress that included lots of volume, a huge bow, and a princess-worthy blue hue that looks plucked straight from Walt Disney's Cinderella. She added silver pumps to the full-on royal look and finished everything off with sparkling, dangling earrings, because in the '80s, more was definitely more. Tim Graham/Getty Images Princess Diana Wore the Most Gloriously '80s Dress to the Premiere of When Harry Met Sally Things were decidedly more low-key a decade later, when Diana attended an event in Birmingham in a houndstooth suit. Though the event happened back in 1995, the look is very now, from the graphic print to the architectural tailoring. It could be something from modern-day Alexander McQueen, proving that Princess Diana's style manages to look fresh no matter what the prevailing trends may be. The look includes statement pockets, a keyhole cutout, and very interesting seams that give the illusion of a bolero and strong shoulder. It's a cerebral look for a princess that stuck to classics more often than not. Tim Graham/Getty Images The Poofy Dress Trend That's All Over Instagram Was Actually Inspired by Princess Diana A year later, Diana would find herself Down Under again. This time, she was attending The Victor Chang Cardiac Research Institute Dinner Dance At The Sydney Entertainment Centre in a sleek, monochrome, one-shoulder dress that could steal the spotlight at a red carpet today. She kept everything blue, from her T-strap pumps to her clutch, and topped the look off with a delicate pearl bracelet and a pair of matching drop earrings.