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How To Pull Off The Classic Jean-on-Jean Look

Six tips to help you embrace the double denim Canadian tuxedo.

Everyone from Rhianna to Gigi Hadid, Selena Gomez to Cindy Crawford has sported the jean-on-jean look — plus, perhaps most famously, Britney Spears and Justin Timberlake, both of whom rocked the fashion world when they sported the groundbreaking ensemble at the 2001 American Music Awards. 

And yet, the pairing of these two staples has somehow not made it fully into the mainstream. Sure, some embrace it. But there are still a whole lot of doubters who fear it’s a “faux pas.” 

If you’re part of the first group, we’ve got some tips that’ll up your game big time. And for all the hmmm, I’m not so sure folks, we’re here to convince you.

History of the “Canadian tuxedo”

It was 1951. Bing Crosby was at the height of his singing career when he visited Vancouver. After a brief hunting trip, he made his way to the high-end Hotel Vancouver to check in. Not recognizing Crosby, hotel staff promptly turned him away because of his denim-on-denim Levi’s ensemble, which was far too casual and not nearly “sophisticated” enough. It was only when a bellhop recognized Crosby that the “misunderstanding” was remedied. Back in the US, Levi’s was LOVING IT. Designers at the iconic brand proceeded to create a custom jean tuxedo for Crosby complete with an interior leather patch that not-so-subtly read: “Notice to all hotel men.” 

Albeit more of a social commentary than a style one, the denim outfit — dubbed the Canadian tuxedo — was nonetheless born.

Six tips to help you embrace the jean-on-jean look

01 Opt for different shades of denim

Otherwise, it’s too “matchy-matchy” (and not nearly as fun). We’re big fans of dark-wash blue jeans on the bottom and light-wash denim up top. Alternatively, go for a different color entirely with a white denim jacket and light or darker wash jeans.

02 Don’t be afraid of distressed details

Contrast is the name of the game here, and a distressed, ripped jean look will work wonders to naturally divide the silhouette.

03 Pair black jeans with a black denim jacket

Okay, so this is technically a riff on the classic Canadian tuxedo, but we couldn’t NOT include it. Layer a white tee underneath the jacket for an edgy, street-style, double denim look that’ll take you from brunch to the bar. Together, these denim pieces pair with booties, tall leather boots, or a class pair of leather loafers.

04 Play around with different jean styles

When most people think jean-on-jean, they envision skinny jeans (for good reason). But there are so. many. other. fashion-forward possibilities to play around with, including:

  • Straight leg
    A close cousin to everyone’s favorite skinny jeans. The main difference? The width of the hem. Straight leg jeans don’t taper inward at the ankles. Instead, the hem remains straight from hip to ankle for a comfortable, vintage-esque silhouette with more breathing room.
  • Slim fit (aka bootcut)
    Just a tad less tight than skinny jeans. They won’t feel like a second skin hugging your body, but they’ll still be form-fitting around your legs and hips (except for a narrow ankle opening).
  • Boyfriend jeans
    Boyfriend jeans take a cue from the relaxed, masculine look. Although they’re, by definition, a bit slouchy, that doesn’t mean they’re not sleek. In fact, more and more brands are designing boyfriend cuts with a slight taper to lend the look a touch more structure. 
  • Flared cut (bell bottoms)
    The ultimate throwback, this cut — which widens starting at the knee and flares outward just above the ankle — was initially popular in the 1960s during the hippie era and is now back with a vengeance. Think of it as the opposite of a skinny jean, with flare that can vary from subtle to exaggerated. 
  • Mom jeans
    High-waisted, relaxed-fit jeans with ample space around the zipper and crotch area. No stone washing. No fading. 

If you have any of these jeans in a high-waisted cut, experiment with a cropped denim jacket.

Read more: 7 Types Of Jeans For Women: A Complete Guide

05 Jean jackets are great, but don’t forget about chambray shirts

This button-down shirt, which is woven differently from denim for a lighter, airier feel, looks fab when tucked into a pair of jeans — especially summery white jeans.

06 Experiment with denim blazers (don’t knock it ‘till you try it)

Whether you opt for sleek & fitted or maxi & oversized, denim blazers pair beautifully with denim jeans. It’s the perfect business-casual look that, depending on shoes and accessories, can lean more towards workwear or “going out” wear.

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