Oprah Winfrey to Kim Kardashian: How Bing Crosby impressed the ‘Canadian tuxedo’ as stars maintain the pattern alive

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  • April 19, 2026
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The Canadian tuxedo has been round because the Fifties and continues to be as fashionable as ever.

Legend has it that the time period Canadian tuxedo was born after Bing Crosby was denied entry to an upscale resort in Vancouver, Canada for being underdressed, as he was carrying a denim on denim outfit designed by the favored denims model, Levi.

After listening to about Crosby’s scenario, Levi Strauss & Co. designed a full denim tuxedo for the singer, so he would by no means be accused of being underdressed once more.

Since then, the denim on denim look has been dubbed the Canadian tuxedo and has been worn by numerous celebrities, together with Oprah Winfrey and Kim Kardashian, each on and off the purple carpet.

Bing Crosby originated the Canadian tuxedo within the Fifties. (Jack Albin/Archive Photographs/Getty Photographs)

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Listed below are a few of the stars who’ve rocked a Canadian tuxedo

Oprah Winfrey

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

Winfrey was photographed sporting a Canadian tuxedo whereas out in New York. (XNY/Star Max/GC Photographs)

Oprah Winfrey was noticed waving at followers whereas out and about in New York Metropolis in a denim outfit.

The discuss present host wore a pair of high-waisted denims which flared out on the backside, which she paired with a unfastened denim jacket with puffy sleeves and gold buttons.

She paired the look with dangling gold earrings, a pair of sun shades and a brown purse, styling her brown hair in huge curls.

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 fairly the assertion once they walked the purple carpet on the AMAs in matching denim outfits. (Frank Trapper/Corbis by way of Getty Photographs)

Justin Timberlake and Britney Spears introduced the Canadian tuxedo again into the mainstream once they posed for pictures on the 2001 American Music Awards.

Spears wore a floorlength strapless denim gown, which she paired with a denim purse, a silver chain round her waist, and silver jewellery, together with an announcement necklace and bracelets.

Timberlake additionally wore head to toe denim, together with a denim cowboy hat and jacket, which he paired with a pair of sun shades and a silver necklace.

“It was such a no brainer. Justin and Britney have been courting on the time. We have been in New Orleans when Britney and Justin have been like, ‘We’re doing matching denim.’ And I used to be like, ‘How are you doing that? Who’s doing that?'” designer Steven Gerstein advised Jezebel in October 2022.

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“It was form of like their promenade,” he added. “They’d an thought, and we did what they wished versus the opposite means round…The remainder is historical past.”

Katy Perry

Katy Perry seen leaving her London Hotel in July 2024.

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

Katy Perry introduced a darker take to the denim on denim pattern when she stepped out of her London resort in 2024.

The “California Ladies” singer was photographed leaving her resort wearing darkish denim pants and an identical jacket, which she paired with black sun shades and open-toed sneakers.

This is not the one time Perry has rocked the Canadian tuxedo, as she has been noticed sporting the look each on and off the purple carpet up to now, even recreating Spears’ iconic AMA second.

“That second Britney gave us was the second, and I wished to pay my respects,” she mentioned about her personal denim purple carpet second on the 2014 VMAs.

Bella Hadid

Bella Hadid in a denim outfit while out in Paris, France in March 2020.

Hadid seemed effortlessly stylish in a denim set whereas out and about in Paris, France. (Marc Piasecki/GC Photographs)

Bella Hadid put her personal spin on the denim on denim look, whereas out and about in Paris, France in 2020.

The supermodel was photographed within the metropolis of affection carrying dishevelled denim denims, which she paired with an outsized fleece-lined denim trench coat with a brown crop prime beneath, giving a touch of midriff.

She paired the look with black sun shades and black square-toed sneakers, and styled her lengthy brown hair with two microbraids to border her face.

Anne Hathaway

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

Hathaway made an announcement when she arrived to the CFDA Trend Awards in a denim prime and skirt. (ANGELA WEISS/AFP by way of Getty Photographs)

Anne Hathaway had a denim second when she posed for pictures on the CFDA Trend Awards in November 2023.

The “Princess Diaries” star turned heads on the purple carpet in a flooring size light-wash denim skirt with floral designs printed on all through, which she paired with a darker strapless denim corset prime with buttons going up the torso.

She paired the outfit with a comfortable make-up look and dazzling Bulgari jewellery, together with a big assertion necklace, bracelets and earrings.

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Dua Lipa

Dua Lipa in a denim crop top in New York City in March 2022.

Dua Lipa introduced a contemporary twist to the Canadian tuxedo whereas out in New York in 2022. (Raymond Corridor/GC Photographs)

Singer, Dua Lipa, introduced a contemporary twist to the Canadian tuxedo when she was photographed for a day trip in New York.

The singer stepped out in a denim bustier prime which confirmed off her toned abs, which she paired with patterned denims with built-in heels, combining two developments in a single.

Dua Lipa accessorized the look with an identical denim purse, a low-slung belt and diamond jewels, together with earrings, bracelets and a necklace.

Emily Ratajkowski

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

Ratajkowski seemed modern as she walked round in Soho in a denim outfit. (Raymond Corridor/GC Photographs)

Emily Ratajkowski surprised when she was noticed sporting a Canadian tuxedo whereas out and about in New York Metropolis.

The mannequin was photographed in a pair of straight-legged high-waisted denims, which she paired with an identical button-up collared denim shirt.

She accessorized with a woven brown belt to interrupt up the denim, which matched her brown sneakers.

Jennifer Lopez

Jennifer Lopez at a screening

Jennifer Lopez surprised in a denim take a look at a particular screening for her film, “Hustlers,” in New York in 2019.

The actress and singer wore a pair of darkish wash denim Balmain denims with a folded waistline and a dropped crotch and cargo-style pockets, which she paired with an identical strapless prime.

She accessorized the look with huge hoop earrings, a diamond necklace and bracelets and clear high-heeled sneakers. She styled her hair in a half-up-half-down look and sported a heavy make-up look with daring lashes.

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Kim Kardashian

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

Kardashian surprised in a novel tackle the Canadian tuxedo with denim pants that changed into navy leather-based chaps. (ANGELA WEISS/AFP by way of Getty Photographs)

Kim Kardashian turned heads when she walked the purple carpet on the WSJ Innovator Awards in November 2019 in a customized Burberry look.

The “Holding Up with the Kardashians” star wore an off-the-shoulder denim corset prime with puffy sleeves and boning on the torso, and a pair of denims which transitioned into navy leather-based chaps.

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She paired the look with blue high-heeled boots which matched the navy chaps. Kardashian let the outfit do all of the speaking, holding her equipment to a minimal and going for a extra subdued make-up look.

Megan Fox

Megan Fox and Machine Gun Kelly leaving

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

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The “Teenage Mutant Ninja Turtles” star was photographed together with her former fiancé, Machine Gun Kelly, whereas leaving “Jimmy Kimmel Stay,” in a pair of dishevelled ripped denim denims, a glittery silver prime and a jean jacket.

Katie Holmes

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

Holmes seemed effortlessly cool as she paired her denim items with a cream cardigan and black undershirt. (Raymond Corridor/GC Photographs)

Katie Holmes is thought for her effortlessly cool model, and her tackle the Canadian tuxedo is not any totally different.

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When attending the Alice + Olivia style present in February 2024, the “Dawson’s Creek” actress wore a pair of dishevelled denims, with a denim button up in a barely brighter shade of blue.

The “Batman Begins” star accessorized the denim look with a black undershirt, a cream jacket and scorching pink sneakers, in addition to a easy gold chain and a white purse.

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