It’s hard to believe it’s been 20 years since Miley Cyrus burst onto the scene with the premiere of “Hannah Montana” on Disney Channel in 2006. The actress and singer-songwriter has displayed quite the style transformation since then, from the colorful layering of her “Hannah Montana” era to edgy looks at awards shows in the modern day. At many points through her style journey, her country roots have come through, including in her footwear choices.
Born and raised in Tennessee with her father Billy Ray Cyrus, who played a similar role as her dad on “Hannah Montana,” and counting Dolly Parton as her godmother, the younger Cyrus was brought up with strong ties to country music. The connection is still present in the 2020s — recall her Grammy-winning “II Most Wanted” duet on Beyoncé Knowles Carter’s 2024 “Cowboy Carter” album. Unsurprisingly, Cyrus has often donned cowboy and Western boot styles to complete her wide-ranging ensembles through the years — FN rounds up a handful below.
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A regular at Hollywood premieres in the 2000s, Cyrus supported her “Hannah Montana” costar Mitchel Musso at the “Monster House” premiere in a boho-country look featuring a flowing white tank, denim shorts and white cowboy boots with a scalloped shaft and pull tabs.
At the “Pirates of the Caribbean: Dead Man’s Chest” premiere, Cyrus wore a red dress with colorful neckline embroidery; the look was completed by brown knee-high boots with an almond toe and modest heel. The Western aura came from decorative detailing along the boots.
Cyrus performed at the Hollywood Radio & Television Society’s Kids Day 2006 event in a gold top with an intricate pattern, dark blue skinny jeans and metallic cowboy boots.
Cyrus took on hosting duties at the 2008 Teen Choice Awards. She displayed a playful Western boot look at the event, a cobalt blue suede style with fringe along the shaft; the boots accented a sequined miniskirt and graphic T-shirt.
Cyrus performed her song “Malibu” at the 2017 Billboard Music Awards wearing a breezy beach-meets-rodeo look including a white off-the-shoulder top and white cut-offs with an embellished belt. The look was completed by a cowboy hat and unzipped ankle boots with a block heel and a heavily distressed, lived-in effect for the upper.
For a Los Angeles outing in 2019, Cyrus added a Western touch to a laid-back ensemble consisting of a T-shirt and biker shorts. She wore a classic cowboy boot featuring red decorative stitching against a black backdrop.