The Most Iconic Denim Looks from the Past 25 Years

From Keira Knightley's low-rise pants to Taylor Swift's skinnies and all the way up to today's blue jean gowns, these are the most influential denim looks from the past two decades

Trends come and go, but denim is forever.

Blue jeans, jean jackets, jean dresses (and insert pretty much any article of clothing you can slap the word "jean" in front of) are the pieces that we, PEOPLE style editors, and most likely you, PEOPLE readers, have in common with a few of Hollywood's best-dressed stars.

Denim has been around for centuries, but only in the past 100 years has it become a fashion power player in pop culture, dating back to when James Dean wore his blue jeans in Rebel Without a Cause.

Since then, there's been many moments when the timeless fabric has been the centerpiece of the most memorable looks in celebrity fashion.

So, we decided to round up the most iconic denim outfits from the past 25 years, from the naughty styles of the early 2000s to today's revamped Canadian tuxedo and everything in between.

Christina Aguilera at the 2001 MTV Video Music Awards

Christina Aguilera was all over the denim trend in the early aughts.

The pop star, who was a fan of liberating her abs at the time, wore low-rise patchwork jeans and a matching newsboy hat to the 2001 MTV Video Music Awards, a moment that made a case for matching your pants to your accessories.

Aguilera told Vogue in 2022 that, during that time, she "starting to come into expressing who I was, having a little bit of fun and not feeling so boxed in."

Keira Knightley at the 2003 'Pirates of the Caribbean' Premiere

Keira Knightly was another star who wasn't shy about flashing her midriff for the cameras.

At the 2003 Pirates of the Caribbean world premiere at Disneyland, her blinged-out belly button made an appearance thanks to her skin-baring outfit, which consisted of the lowest of low-rise jeans and an off-the-shoulder bandage top. She dialed down the sex appeal with a regal pearl necklace.

Janet Jackson at the 2006 ESPY Awards

All eyes were on Janet Jackson in the early 2000s, who was just as much as a style icon on stage as she was on the red carpet.

One of her best looks from 2006 happened at the ESPY Awards, where she wore a denim halterneck mermaid dress accentuated with an ultra waist-snatching belt. The look couldn't have been more '000s, especially with Jackson's brown suede heels and super high ponytail.

Cameron Diaz at a 'Bad Teacher' Photocall in 2014

One defining clothing item of the mid-2000s was jeggings (dun, dun, dun).

The legging-jean hybrid took over department stores and mall kiosks in the 2010s as soon as people realized that a sexy pair of skinny jeans — which were gaining traction again — didn't have to be so uncomfortable (read: required squats to stretch out the pant legs) after all.

Jeggings became such a hot item that even high-end brands were incorporating them into their collections, which is how they ended up on stars like Cameron Diaz, who wore a pair of J Brand 901 light-wash leggings to the Bad Teacher photo call in Moscow in 2011. She teamed her pair with a Chanel jacket and red Casadei heels.

Taylor Swift in London in 2012

Taylor Swift has many memorable red carpet moments in her resume, but her off-duty street style over the years has been just as influential.

Take this 2012 look, which was the textbook definition of 2010s style. On a stroll in London, the pop star, then in her skinny jeans era, bundled up in a maroon duffle coat (a likely Easter egg for her album Red, which would release in October that year) and ankle-length jeans with little give. The loafers and satchel epitomized the popular preppy style at the time.

Katy Perry at the 2014 MTV Video Music Awards

Katy Perry arrived at the 2014 MTV Video Music Awards in a Western getup inspired by Britney Spears, who put her own pop star spin on the Canadian tuxedo back in 2001, when she and Justin Timberlake matched in denim at the American Music Awards.

Perry's version consisted of a studded Versace patchwork denim dress, which was custom-made for the "Roar" singer, but still had the essence of Spears' Kurt and Bart gown (they both had sweetheart necklines and mermaid silhouettes).

Perry's date, rapper RiFF RAFF, was even the Timberlake to her Spears, as he was also decked out in a jean suit and cowboy boots. Everything about it, Perry told PEOPLE in 2022, was "so iconic."

Kendall Jenner at the 2017 Cannes Film Festival

The Cannes Film Festival usually involves multiple outfit changes from the stars who attend the premieres and parties held during the weeks-long festivities. When Kendall Jenner returned to Cannes in 2017, she rocked three red carpet gowns — and one unexpected denim look.

For the Fashion for Relief event, the supermodel wore an Alexandre Vauthier couture wrap top with a dramatic train and one statement sleeve. The high-low design of the shirt really accentuated her high-waisted cutoff shorts, which added a laid-back Calabasas vibe to the French glamour of it all.

Rihanna in London in 2013

Even though skinny jeans were all the rage in the 2010s, baggy styles had a moment too.

Rihanna often stepped out in loose-fitted denim that fit into her effortlessly cool wardrobe. The singer mastered the art of double denim with these optical illusion boyfriend jeans, which had the appearance of '80s mid-wash high-rise pants with a 2000s low-rise silhouette combined into one.

Meghan Markle at the 2017 Invictus Games

Meghan Markle and Prince Harry made their first public outing at the 2017 Invictus Games in Toronto, one year after their relationship was catapulted into the public eye.

The couple's PDA stirred a lot of buzz, as did Markle's preppy outfit, which she styled with a crisp blue oxford button-up and distressed skinny jeans. Though she would soon become the Duchess of Sussex following her marriage to Prince Harry in 2018, she'd remain loyal to her signature chic business-casual uniform.

Anne Hathaway at the 2023 CFDA Awards

Since Anne Hathaway entered a new style era in 2022, we've been keeping track of every look she's worn on and off the red carpet.

The Oscar-winning star has incorporated denim into high-fashion ensembles on a few occasions, whether it be in the form of a classic denim jacket thrown over a sequin gown or the everyday jean. But she pulled off her boldest denim look at the 2023 CFDA Awards, wearing this spring/summer 2024 Ralph Lauren two-piece set featuring a patterned corset and floor-sweeping skirt.

Katie Holmes at Z100's 2022 iHeartRadio Jingle Ball

Katie Holmes has stepped out in quite a few contemporary denim looks, but nothing broke the Internet quite like when she wore a mini (and we mean mini) strapless corset dress over a pair of loose straight-leg jeans with distressed hemming to Z100's iHeartRadio Jingle Ball concert in 2022.

The layered outfit, which also included dad sneakers, was unexpected for the actress and mom and sparked quite a debate online. But in an April 2023 interview on The Drew Barrymore Show, Holmes said she thought she "looked cool" and never expected for the outfit to go viral.

Ice Spice at the 2024 Grammys

Gen Z stars have made it their mission to wear archival designer clothes that are way older than them. Take Ice Spice for example, who made her Grammys debut in custom Baby Phat this past March.

The rapper definitely wasn't around when Kimora Lee Simmons launched her brand in 1999, a year before she was even born. But she made a nostalgic nod to the Y2K brand and the decade's obsession with denim in a dark-wash jean jacket trimmed with fur and a matching skirt.

Da'Vine Joy Randolph at the 2024 Met Gala

The 2024 Met Gala theme centered around recycling what is old and making it new again. Da'Vine Joy Randolph, who made her debut at fashion's biggest night in May, nailed the assignment by reintroducing the fabric in a new way.

The Holdovers actress hit the carpet in a custom gown which a sprawling multi-wash pleated train and bell sleeves. Randolph said the dress made her "fall back in love with denim" and we couldn't agree more.

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