Herbootz.com : SOCIAL AF

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See How Diana Ross, Marilyn Monroe & More Styled Western Boots Through the Years

kendall jenner, fendi spring 2019, milan fashion week
Kendall Jenner exiting the Fendi spring ’19 show on Sept. 20, 2018 in bold teal Western boots by the Italian label.

At Paris Haute Couture Fashion Week in January, Schiaparelli teamed the boots with elegant frocks. Victoria’s Secret Angel Taylor Hill worked the runway in a hot-pink minidress that was surprisingly paired with Western boots.

Schiaparelli , taylor hill, runway, couture, western boots
Taylor Hill on the catwalk at the Schiaparelli couture show for spring ’19.

But while the trend has reemerged in full force in recent seasons, Western boots are not new to fashion.

Ralph Lauren was the first one to take the American heritage style and make it a high-fashion must-have. At a 1979 gala, Lauren sent models down the runway in high-waisted pants and the must-have shoes. Models added bandanas and cowboy hats as accessories and sashayed on the catwalk with hands on hips.


In the early 1980s, cowboy boots were a surprising fashion staple that moved far beyond the American West. A 1980 photo of Motown legend Diana Ross shows the singer sprawled out in a petal-pink jumpsuit and high-heeled white Western boots with fringe detailing.

DIANA ROSS, western boots, celebrity style, VARIOUS - 1980
Diana Ross sports a pale-pink jumpsuit with white high-heeled Western boots.

Perhaps one of the most memorable Western boot moments of all time came courtesy of Princess Diana. The royal stepped out in 1989 to pick up her youngest son, Prince Harry, while clad in a black blazer and sweatpants. She finished her surprising look with brown cowboy boots and a navy baseball cap.

Princess Diana, cowboy boots, sweatpants, blazer, baseball cap, Prince Harry going back to school, Britain - Apr 1989
Princess Diana wears cowboy boots with sweats in 1989.

Click through the gallery to see more major Western boot moments through the years.

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