Princess Diana's Old Styling Trick Is Suddenly Everywhere

It's been 30 years, but we haven't forgotten that Princess Diana famously tucked both her jeans and sweats into Western boots. That's why when we saw the trend pop up on the Fall 2019 runways and simultaneously on the street, we deemed it iconic. It's the perfect example of a cyclical trend that's already been adopted by Kendall Jenner, followed by the rest of the fashion world.

Diana was spotted pulling off the look at the polo club and dropping off her kids from school in the late 1980s, and we love the way the style was reinterpreted at Alberta Ferretti and even Rachel Comey, with a red zippered bootie. Presumably though, you'd like to translate this move for your own wardrobe, so we're showing you exactly how it's done. Read ahead for a full lesson in the Diana boot tuck.

Princess Diana Wearing Jeans Tucked Into Boots in 1988
Getty | Tim Graham

Princess Diana Wearing Jeans Tucked Into Boots in 1988

Princess Diana Wearing Jeans Tucked Into Her Sweats in 1989
Getty | Tim Graham

Princess Diana Wearing Jeans Tucked Into Her Sweats in 1989

See the Boot Tuck on the Fall 2019 Runways
IMAXTREE | Salvatore Dragone

See the Boot Tuck on the Fall 2019 Runways

Maryam Nassir Zadeh Fall 2019

IMAXTREE | IMAXTREE.COM

Khaite Fall 2019

IMAXTREE | Salvatore Dragone

Alberta Ferretti Fall 2019

How to Wear the Boot Tuck on the Street
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How to Wear the Boot Tuck on the Street

Tuck your nylon sport pants into knee-high cowboy boots, and keep it cozy on top in a crew neck sweatshirt à la Kendall Jenner.

Style Du Monde

Tuck tapered leather trousers into a slick sock bootie.

Style Du Monde

Amplify your Western-inspired look with a Canadian tuxedo.

Style Du Monde

Try tucking leopard skinnies into edgy, studded knee-high boots.

Style Du Monde

Slip your slouchy silk track pants into your go-to cowboy boots, and complete with a puffer.

Style Du Monde

Accessorize the look with a bandana, and cinch your waist with a belt to define your figure.