An oversized college sweatshirt, black biker shorts, sneakers and chic black sunglasses are one of the most popular street style combos of 2020, but never forget—Princess Diana was the true trendsetter, and she did it first.

In what is perhaps one of her most iconic and underrated looks, Princess Diana dons an all-white suit and black bow-tie with glossy heels and sheer tights during a trip to Florence.

The Princess of Wales steps out to a fashion show in London in a one-shoulder, electric blue Bruce Oldfield dress with circular motifs.

In an iconic, eclectic patterned fringe coat with contrasting blue accessories, Diana dons a fun look after announcing her first pregnancy in London.

Like a princess from a true fairy-tale, Diana wears a gorgeous baby blue off-shoulder chiffon gown with a matching fabric choker at the red carpet of Cannes Film Festival in 1987.

At a White House dinner in 1985, Princess Diana dances with John Travolta in the iconic black "Travolta dress."

In an elaborate wedding dress designed by Emanuel, Princess Diana celebrates her new, royal marriage in St. Paul's Cathedral.

Princess Diana pairs a chic black taffeta dress with a diamond tennis bracelet and necklace at a London fundraising concert in 1981.

In a look fit not only for a princess but most definitely a queen, Princess Diana wears a billowing, floor-length red gown with an attached cape.

In an all-black "revenge dress" ensemble, Lady Di struts this form-fitting iconic outfit after Prince Charles confessed his adultery.