Princess Diana wears a floral-print strapless gown and white kitten heels to the 1988 premiere of “Crocodile Dundee.”
Meghan Markle shows off her curves in a trumpet-style gown at the 2014 Elton John AIDS Foundation gala.
Pictured in 1995, Princess Diana channels Jacqueline Kennedy Onassis in a pink two-piece suit and pillbox hat.
Meghan Markle accessorizes her graphic-print skirt with strappy black sandals at the 2014 NBC Universal Winter Press Tour.
Two-tone heels perfectly complement Princess Diana’s nautical-inspired look at the 1987 Cannes Film Festival.
At the 2016 Women in Television Dinner, Meghan Markle wears an Asian-inspired brocade minidress and delicate pointy-toe pumps.
Princess Diana makes a bold statement in a colorblock dress and matching hat during a 1989 tour of the Middle East.
Meghan Markle bundles up in a double-breasted coat, accessorized with black pumps, at the 2018 Anzac Day Dawn Service in London.
Princess Diana wears bold stripes and coordinating cap-toe heels to the 1997 Ely Cathedral Flower Festival in Cambridgeshire, England.
Meghan Markle (pictured with Prince Harry) looks effortlessly chic in a Hugo Boss belted dress and nude pumps at the 2018 Stephen Lawrence Memorial.