Princess Diana’s Most Unexpected Fashion Flops Before They Became Royal History

Princess Diana wore a black satin Emanuel dress during her first official public engagement with Prince Charles in 1981. The black Emanuel dress was reportedly considered inappropriate and too dour for the event due to its dark color and form-fitting, shoulder-baring shape.

Over the years, Princess Diana became one of the most influential figures of the time. From elegant evening gowns to her relaxed and casual off-duty looks, Diana’s sartorial choices always remained a topic of conversation.

That said, sometimes even the late Princess got it wrong. A few fashion critics and stylists have opined that some of Diana’s outfits missed the mark or did not come together as the royal might have intended.

While the silhouettes sometimes seemed off, other times her fabric choices were not the best.

Designer Elizabeth Emanuel described Princess Diana as “a true sweetheart with not a lot of knowledge about fashion.”

Here’s a look at a few of Princess Diana’s most “questionable” outfits from her time as a royal.

Princess Diana’s Tweed Kilt “Suit” From Her Honeymoon in 1981

Princess Diana opted for a traditional tweed suit during her honeymoon in Scotland with the then-Prince, King Charles, in 1981. While tweed remains a timeless fabric in fashion, it can be tricky to style.

Speaking of which, some fashion critics believe that Diana’s tweed suit, designed by Bill Pashley, looked “frumpy” and reminded one of a school uniform from the ’80s.

Princess Diana’s Black Lace Dress When Meeting the Pope in 1985

While black is usually reserved for more solemn events like funerals, Diana chose to wear a black lace dress and veil by Catherine Walker to her meeting with Pope John Paul II at the Vatican in 1985.

The Nigerian State Banquet, 1989

Princess Diana wore a plaid number at the Braemar Games in Scotland. The royal also donned the Spencer family tiara on the occasion. Keeping with the trend of the times, Diana chose to go big on the accessories with a big hat, big buttons, and a big collar. However, too many accessories might have done the Princess a disservice.

Prince William’s Birth, 1982

On the special occasion of presenting her firstborn and the Future King, Prince William, to royal watchers, Diana wore a green spotted outfit that featured a white pussy-bow. Again, while the apparel of choice might have been in sync with the decade’s trends, according to the NZ Herald, “it looks like something wee William’s grandmother would wear to bed.“

The 1986 Windsor Polo Match

During the Polo match in Windsor in 1986, critics believe that Princess Diana opted for a questionable outfit, even by common people’s standards: a sweater over a spotted skirt, paired with spotted socks.

Like anyone else, Princess Diana’s style changed over time. Irrespective of her rare fashion flops, she continued to inspire people with her taste and elegance throughout the years.