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Oprah Winfrey, Kim Kardashian and more celebrities who rocked a Canadian tuxedo

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The Canadian tuxedo has been around since the 1950s and is still as fashionable as ever.

Legend has it that the term Canadian tuxedo was born after Bing Crosby was denied entry to a luxury hotel in Vancouver, Canada, for being scantily clad in a denim-on-denim outfit designed by the popular denim brand Levi.

After hearing about Crosby’s situation, Levi Strauss & Co. designed a full denim tuxedo for the singer so he would never again be accused of being underdressed.

Since then, the denim-on-denim look has been dubbed the Canadian tuxedo and has been worn both on and off the red carpet by countless celebrities, including Oprah Winfrey and Kim Kardashian.

Bing Crosby created the Canadian tuxedo in the 1950s. (Jack Albin/Archive Photos/Getty Images)

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Here are some of the stars rocking the Canadian tuxedo

Oprah Winfrey

Oprah Winfrey while out in New York in April 2026 wearing a denim outfit.

Winfrey was photographed wearing a Canadian tuxedo in New York. (XNY/Star Max/GC Images)

Oprah Winfrey was spotted waving to fans while out in New York City in a denim outfit.

The talk show host wore a pair of high-waisted jeans that flared at the bottom and paired it with a loose denim jacket with puff sleeves and gold buttons.

She styled her brown hair into big curls, pairing the look with dangling gold earrings, a pair of sunglasses, and a brown bag.

Britney Spears and Justin Timberlake

Britney Spears and Justin Timberlake in matching denim outfits at the AMAs in January

Britney Spears and Justin Timberlake made quite the statement as they walked the AMAs red carpet in matching denim outfits. (Frank Trapper/Corbis via Getty Images)

Justin Timberlake and Britney Spears posed for photos at the 2001 American Music Awards, bringing the Canadian tuxedo back into the mainstream.

Spears wore a floor-length strapless denim dress and paired it with a denim bag, a silver chain around her waist, and silver jewelry, including a statement necklace and bracelets.

Timberlake also wore head-to-toe denim, including a denim cowboy hat and jacket, and paired them with a pair of sunglasses and a silver necklace.

“It was a very simple thing. Justin and Britney were dating at the time. When we were in New Orleans, Britney and Justin said, ‘We do matching denim.’ And I said, ‘How do you do that? Who does that?'” said designer Steven Gerstein. Jezebel In October 2022.

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“It was kind of like their prom,” he added. “They had an idea and we did what they wanted, and the opposite happened… The rest is history.”

katy perry

Katy Perry was seen leaving her hotel in London in July 2024.

Perry wore a Canadian tuxedo while exploring London. (Ricky Vigil M/Justin E Palmer/GC Images)

Katy Perry put a darker spin on the denim on denim trend when she left her hotel in London in 2024.

The “California Girls” singer was photographed leaving her hotel wearing dark jeans and a matching jacket, which she paired with black sunglasses and open-toed shoes.

This isn’t the only time Perry has rocked a Canadian tuxedo; She’s been seen rocking sporty looks both on and off the red carpet in the past, even recreating Spears’ iconic AMA moment.

“That was the moment that Britney gave us, and I wanted to pay tribute,” she said of her own denim red carpet moment at the 2014 VMAs.

Bella Hadid

Bella Hadid walking around in denim in Paris, France, in March 2020.

Hadid looked effortlessly chic in her denim set while out and about in Paris, France. (Marc Piasecki/GC Images)

Bella Hadid added her own style to the denim-on-denim look while wandering around Paris, France in 2020.

The supermodel was photographed wearing baggy denim jeans in the city of love, which she paired with an oversized, fleece-lined denim trench coat and a brown crop top underneath, giving a hint of midriff.

She paired the look with black sunglasses and black square-toe shoes and styled her long brown hair in two micro braids to frame her face.

Anne Hathaway

Anne Hathaway in a denim dress at the CFDA Fashion Awards in New York in November 2023

Hathaway made a statement when she arrived at the CFDA Fashion Awards in a denim top and skirt. (ANGELA WEISS/AFP via Getty Images)

Anne Hathaway had a jeans moment while posing for photos at the CFDA Fashion Awards in November 2023.

The “Princess Diaries” star turned heads on the red carpet in a floor-length light-wash denim skirt with an all-over floral print, which she paired with a darker strapless denim corset top with torso-length buttons.

She paired her outfit with a soft makeup look and dazzling Bulgari jewelry, including a chunky necklace, bracelets and earrings.

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“Everyone is taking risks right now and I feel like there’s more than one way to do it, which means you don’t have to achieve a goal, you just have to be yourself and that’s a great feeling,” Hathaway said. People In 2023, she talked about how her stylist Erin Walsh made her comfortable with taking fashion risks.

Dua Lipa

Dua Lipa in her denim crop top in New York in March 2022.

Dua Lipa brought a modern twist to the Canadian tuxedo while in New York in 2022. (Raymond Hall/GC Images)

Singer Dua Lipa put a modern twist on her Canadian tuxedo while being photographed for a day out in New York.

The singer hit the stage in a denim bustier top that showed off her toned abs, and paired it with patterned jeans with built-in heels, bringing the two trends together.

Dua Lipa accessorized the look with a matching denim bag, a low-slung belt, and diamond jewelry, including earrings, bracelets, and a necklace.

Emily Ratajkowski

Emily Ratajkowski while out in Soho in November 2021 in a denim outfit.

Ratajkowski looked chic while strolling around Soho in a denim outfit. (Raymond Hall/GC Images)

Emily Ratajkowski stunned when she was spotted wearing a Canadian tuxedo while out and about in New York.

The model was photographed wearing straight-leg, high-waisted jeans, which she paired with a matching button-down collar denim shirt.

She accessorized with a brown woven belt to break up the jeans that matched her brown shoes.

Jennifer Lopez

Jennifer Lopez at a screening

Jennifer Lopez stunned in her denim look at a special screening of the movie “Hustlers” in New York in 2019.

The actress and singer wore dark wash denim Balmain jeans with a folded waist, dropped crotch, and cargo-style pockets, and paired it with a matching strapless top.

She completed her look with chunky hoop earrings, diamond necklace, bracelets and clear high heels. She styled her hair in a half-up, half-down style and sported a heavy makeup look with thick lashes.

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Kim Kardashian

Kim Kardashian at the WSJ Magazine Innovator Awards in November 2019.

Kardashian stunned with her unique interpretation of the Canadian tuxedo with jeans that morphed into navy blue leather pieces. (ANGELA WEISS/AFP via Getty Images)

Kim Kardashian turned heads when she walked the red carpet in a custom Burberry look at the WSJ Innovator Awards in November 2019.

The “Keeping Up with the Kardashians” star wore an off-the-shoulder denim corset top with puff sleeves and bones at the torso, which turned into navy leather pants.

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She paired the look with blue high-heeled boots paired with navy blue trousers. Kardashian let the outfit do all the talking, keeping accessories to a minimum and going for a simpler makeup look.

Megan Fox

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Megan Fox added some sparkle to her version of the Canadian tuxedo.

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The “Teenage Mutant Ninja Turtles” star left “Jimmy Kimmel Live” wearing baggy ripped jeans, a sparkly silver top and a jean jacket while posing for photos with her ex-fiancé, Machine Gun Kelly.

Katie Holmes

Katie Holmes outside the Alice + Olivia fashion show in February 2024.

Holmes looked ultra-cool as she paired her denim pieces with a cream cardigan and black undershirt. (Raymond Hall/GC Images)

Katie Holmes is known for her effortlessly cool style, and her take on the Canadian tuxedo is no different.

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The “Dawson’s Creek” actor wore loose-fitting button-up jeans in a slightly brighter shade of blue while attending the Alice + Olivia fashion show in February 2024.

The “Batman Begins” star completed her denim look with a black undershirt, cream jacket and hot pink shoes, along with a simple gold chain and a white bag.

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