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Slide 22 of 37

Blazers, Baseball Caps, and Boots

Although this is one of Princess Diana's late '80s looks, it more closely resembles her casual '90s style. The princess wore a very American combination of blue jeans, brown cowboy boots, a white t-shirt with the "British Lung Foundation" printed at centre, and a casual black blazer to the Guards Polo Club in 1988.

Image Source: Getty / Tim Graham