13 Iconic Denim Moments That Went Down in Pop Culture History

13 Iconic Denim Moments That Went Down in Pop Culture History
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When it comes to fashion, nothing defines Americans better than denim. In fact, we’d bet that no other material can single-handedly conjure up visions of America and its storied subcultures better than denim: Greasers, cowboys, hippies, rappers, rockers—they all put their own unique stamp on the same staple. And today, we’re just as connected to our own interpretations of denim, if not more so.

MORE: Denim Cheat Sheet: How To Wash Your Jeans, Break Them In, And Fold Them Like a Pro

Considering the sheer prevalence of styles available to us right now, it’s no wonder that—throughout the last decade or so—jeans have emerged as wear-anywhere essentials, as opposed to the basic, casual, anti-establishment staples they once were. From shorts and skirts, to colored and artfully-printed styles—not to mention broken-in jackets, vests, and classic 5-pocket styles, we’ve taken denim to a whole new, staggeringly broad level.

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However, it’s occasionally worth going back to our denim roots to revisit moments that helped cement the humble jean as the celebrated staple they are now. And between Bing Crosby’s custom Levi’s Canadian tuxedo, Calvin Klein’s game-changing ads starring Brooke Shields, Mark Wahlberg and Kate Moss, and Cindy Crawford‘s classic 1991 Pepsi commercial, we have lots to work with.

Click through the gallery above to see 13 iconic denim moments that earned a spot in pop culture!

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Brooke Shields' 1980 Calvin Klein ad. Shot and directed by legendary fashion photographer Richard Avedon, this now-legendary campaign for the newly launched CK Calvin Klein Jeans label shocked due to its sexually provacative nature. It might not seem particulary scandalous by today's standards, but Shields was 15 years old when she shot the ads and commericals, which catapulted the line “You wanna know what comes between me and my Calvins? Nothing" to pop culture fame.

Britney Spears and Justin Timberlake's matching denim outfits at the American Music Awards. Forever ingranied in our memory, the unfortunate "couples denim" incident of 2001 sums up so many things about the early-2000s, and we have to say—we miss those days a little, considering how too-cool-for-school JT has become.

Anna Wintour's first Vogue cover shocked the fashion world when it showcased Israeli model Michaela Bercu wearing jeans and a Christian Lacroix jacket in a street style-esque photo. Typically, the fashion bible covers had been full-on "fashion," and though you can't really see the denim in the photo, it spoke volumes about where fashion was headed, and a nod to personal style.  

Cindy Crawford's 1991 Pepsi commercial. Everything about this TV spot smartly inferred "all American," from the use of the time's biggest supermodel—who pulled up to a dusty roadside stop in a red Lamborghini to get a can of Pepsi—to her outfit of a classic white tank top, bombshell hair, and sexy denim cutoffs.

Bruce Springsteen's 1984 "Born in the USA" album cover. Few rockers can, well, rock a pair of blue jeans quite as well as Springsteen, and he's more than proved he's the boss of denim, often appearing in an appropriately everyman uniform of faded jeans and a white tee. In 1984, he was photographed by Annie Leibovitz for the cover of "Born in the USA," which became an iconic image of the era.  

Bing Crosby's Canadian Tux. Crooner and actor Bing Crosby was a known fan of wearing jeans and jean jackets and—as history tells it—when Crosby approached a Canadian hotel to check in, a clerk wouldn't let him because of his denim ensemble. The reason? As Levi's archivist Lynn Downey has said, denim had a bad reputation in the 1950s thanks to Marlon Brando, James Dean and other brooders "who were upsetting the social order by not conforming to America’s postwar obsession with suburbs, picket fences and men in grey flannel suits. Not only that, [but] denim still retained its workwear, laborer origins."

When the Levi’s found out about Bing's hotel turnaway, they tailored an entirely denim tuxedo for him which became one of his most famous outfits!


The cast of "Beverly Hills, 90210." Perhaps no better '90s event managed to showcase the very real fashions of the decade. From its 1990 inception, every iconic episode was packed with a mix of babydoll dresses, crop tops, bolo ties, and floppy velvet hats, but it was the constant use of light-wash denim on Brandon, Brenda, Kelly, Steve, Andrea, Dylan, David, Donna, and the rest of the gang that we remember most. 

The phenomenon of sagging jeans—which, some theorize, was originated in prison in the 1990s—was appropriated by hip-hop stars, and it became common to see the biggest rappers of the decade (and their fans) wearing boxer-showing baggy jeans. It became even more popular as these rappers began their own clothing labels, or started appearing in campaigns like the one above for '90s streetwear label Cross Colors, which features Death Row labelmates Dr. Dre, Snoop Dogg, and the Dogg Pound

Claudia Schiffer's Guess Jeans Campaigns. The German supermodel starred in six black-and-white campaigns for Guess Jeans between 1989 and 1991, all shot by Ellen von Unwerth. The campaigns were were considered a turning point for both the model and the brand, as she had only recently been discovered in 1989 (and was 19 years old at the time), and the brand was only around eight years old.


Marky Mark and Kate Moss for Calvin Klein. Perhaps the most iconic denim moment of the past few decades, the impact that Calvin Klein Underwear' 1992 ads—starring then-rapper and bad boy Marky Mark and iconic waify supermodel Kate Moss—had on pop culture needs no explanation. 

Versace Jeans Couture Ads. Versace Jeans ads throughout the '90s were known for their slightly suggestive nature, often featuring two female models. This one stars the super-leggy Nadia Auermann and Claudia Schiffer.

Jane Birkin's jeans. The namesake of the Hermès Birkin bag (and the mom of modern-day French fashion muses Charlotte Gainsbourg and Lou Doillon), English actress and singer Birkin has long been considered the queen of jeans. Often photographed throughout the 1960s and '70s in the same pair of faded jeans, Birkin was the pinnacle of easygoing glamour, pairing her denim with staples such as plain white tees, wedge sandals, ballet flats, and striped shirts.

Daisy Duke's Daisy Dukes. "The Dukes of Hazzard" character Daisy Mae Duke—played by actress Catherine Bach—has cememted her place in pop culture due of her outfits of tiny denim shorts, which have colloquially become known as "Daisy Dukes." 

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