15 Ways to Wear Cowboy Boots

Posted by Erma Hippe on Monday, June 3, 2024
1

Old Hollywood Westerns

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Actress Wendy Waldron pairs her cowboy boots with a bra top and high-waisted shorts circa 1949.

2

Marilyn Monroe

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Bringing the boots from the '30s and '40s classic western movies into the 1950s, the iconic Hollywood actress poses for a Valentine's Day photo shoot.

3

Raquel Welch

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The leading lady went full-on Americana in a patriotic swimsuit and white cowboy boots for the film, Myra Breckinridge—giving the classic boot a sexy upgrade.

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4

Studio 54 Nights

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In the early '80s, club-goers at New York's iconic Studio 54 embraced the trend in white with cascading dresses.

5

Pamela Anderson

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Giving it the '90s grunge treatment, the blonde bombshell rocked a pair of black patent cowboy boots with denim cut-offs and a white tee.

6

Daisy Duke's Comeback

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With the 2005 movie remake of Dukes of Hazzard, Jessica Simpson emerged as the new Daisy Duke: denim cut-offs, western belts, and a pair of bright red cowboy boots to top it all off.

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7

The Early Aughts

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The cowboy boot enjoyed a mini revival yet again in the early 2000s—this time gracing the red carpet. From Britney Spears to Sheryl Crow and even Rihanna, the boot made a trendy comeback (though the craze was slightly short-lived).

8

Taylor Swift

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In 2008, country's breakout teenage star made every girl across America want to pair cowboy boots with sundresses.

9

Carrie Underwood

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The country singer rocks her boots both on and off the stage—pairing them with everything from shorts to skirts and dresses.

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10

Beyoncé

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The proud Houston, Texas native doesn't forget to embrace her roots. Pre-Lemonade, the singer shared a series of country-inspired photos on her old site in embroidered cowboy boots, a "Property of Texas" shirt, and cut-offs.

11

Country Strong

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In the 2010 film, Gwyneth Paltrow transformed into a country singer—cowboy boots, guitar, and all.

12

Kate Moss

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The supermodel always manages to upgrade her cowboy boots with a glam fur topper.

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13

The Royal Way

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The Duke and Duchess of Cambridge showed off their penchant for western attire back in 2011 while on a royal trip to Canada in matching cowboy hats and boots with blue jeans.

14

Festival Style

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From Coachella to Lollapalooza and beyond, cowboy boots have proven their stance as the ultimate musical festival must-have for the style set of today.

15

On The Fall 2017 Runways

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From left: Maison Margiela, House of Holland, Calvin Klein

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16

Shop The Look

Footwear, Boot, Shoe, High heels, Durango boot, Beige, Getty ImagesHeadshot of Lauren Alexis Fisher

Lauren Alexis Fisher is the Senior Editor at Cosmopolitan, overseeing digital content across fashion, lifestyle, beauty, sex, and culture. Previously, she was the Market Editor at Harper’s BAZAAR and has written for publications including WWD, Bustle, and W Magazine. When she’s not busy taste-testing her way through every dirty martini in New York, you can follow her on Instagram for bad jokes, good outfits, and annoying vacation pics. 

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