The Most Iconic Denim Looks from the Past 25 Years

Mar. 15, 2025

The most iconic denim looks from the past 25 years.

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 afashion power player in pop culture, dating back to when James Dean wore his blue jeans inRebel 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.

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 afashion power player in pop culture, dating back to when James Dean wore his blue jeans inRebel 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.

01of 13

Da’Vine Joy Randolph at the 2024 Met Gala

Da’Vine Joy Randolph.Dimitrios Kambouris/Getty

Dimitrios Kambouris/Getty

TheHoldoversactress hit the carpet in acustom gown, which featured 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.

02of 13

Ice Spice at the 2024 Grammys

Ice Spice.Gilbert Flores/Billboard via Getty

Gilbert Flores/Billboard via Getty

The rapper definitely wasn’t around whenKimora Lee Simmonslaunched 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.

03of 13Anne Hathaway at the 2023 CFDA AwardsAnne Hathaway.ANGELA WEISS/AFP via GettySinceAnne Hathawayentered 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 theeveryday 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.

03of 13

Anne Hathaway at the 2023 CFDA Awards

Anne Hathaway.ANGELA WEISS/AFP via Getty

ANGELA WEISS/AFP via Getty

SinceAnne Hathawayentered 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 theeveryday 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.

04of 13Katie Holmes at Z100’s 2022 iHeartRadio Jingle BallKatie Holmes.Dia Dipasupil/GettyKatie Holmeshas stepped out in quite a fewcontemporary 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 jeanswith 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 anApril 2023 interviewonThe Drew Barrymore Show, Holmes said she thought she “looked cool” and never expected for the outfit to go viral.

04of 13

Katie Holmes at Z100’s 2022 iHeartRadio Jingle Ball

Katie Holmes.Dia Dipasupil/Getty

Dia Dipasupil/Getty

Katie Holmeshas stepped out in quite a fewcontemporary 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 jeanswith 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 anApril 2023 interviewonThe Drew Barrymore Show, Holmes said she thought she “looked cool” and never expected for the outfit to go viral.

05of 13

Meghan Markle.Karwai Tang/WireImage

Karwai Tang/WireImage

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 Sussexfollowing her marriage to Prince Harryin 2018, she’d remain loyal to her signature chic business-casual uniform.

06of 13Kendall Jenner at the 2017 Cannes Film FestivalKendall Jenner.Samir Hussein/WireImageTheCannes Film Festivalusually involves multiple outfit changes from the stars who attend the premieres and parties held during the weeks-long festivities. WhenKendall Jennerreturned 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.

06of 13

Kendall Jenner at the 2017 Cannes Film Festival

Kendall Jenner.Samir Hussein/WireImage

Samir Hussein/WireImage

TheCannes Film Festivalusually involves multiple outfit changes from the stars who attend the premieres and parties held during the weeks-long festivities. WhenKendall Jennerreturned 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.

07of 13

Katy Perry.Jason Merritt/Getty

Jason Merritt/Getty

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.”

08of 13Rihanna in London in 2013Rihanna.Dave M. Benett/GettyEven though skinny jeans were all the rage in the 2010s, baggy styles had a moment too.Rihannaoften 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.

08of 13

Rihanna in London in 2013

Rihanna.Dave M. Benett/Getty

Dave M. Benett/Getty

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

Rihannaoften 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.

09of 13Taylor Swift in London in 2012Taylor Swift.JJ/Bauer-Griffin/GC ImagesTaylor Swifthas 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 albumRed,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.

09of 13

Taylor Swift in London in 2012

Taylor Swift.JJ/Bauer-Griffin/GC Images

JJ/Bauer-Griffin/GC Images

Taylor Swifthas 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 albumRed,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.

10of 13Cameron Diaz at a ‘Bad Teacher’ Photocall in 2011Cameron Diaz.Alexander Aleshkin/Epsilon/GettyOne 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 likeCameron Diaz, who wore a pair of J Brand 901 light-wash leggings to theBad Teacherphoto call in Moscow in 2011. She teamed her pair with a Chanel jacket and red Casadei heels.

10of 13

Cameron Diaz at a ‘Bad Teacher’ Photocall in 2011

Cameron Diaz.Alexander Aleshkin/Epsilon/Getty

Alexander Aleshkin/Epsilon/Getty

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 likeCameron Diaz, who wore a pair of J Brand 901 light-wash leggings to theBad Teacherphoto call in Moscow in 2011. She teamed her pair with a Chanel jacket and red Casadei heels.

11of 13Janet Jackson at the 2006 ESPY AwardsJanet Jackson.Jeffrey Mayer/WireImageAll eyes were onJanet Jacksonin 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.

11of 13

Janet Jackson at the 2006 ESPY Awards

Janet Jackson.Jeffrey Mayer/WireImage

Jeffrey Mayer/WireImage

All eyes were onJanet Jacksonin 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.

12of 13Keira Knightley at the 2003 ‘Pirates of the Caribbean’ PremiereKeira Knightley.Amanda Edwards/GettyKeira Knightlywas another star who wasn’t shy about flashing her midriff for the cameras.At the 2003Pirates of the Caribbeanworld 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.

12of 13

Keira Knightley at the 2003 ‘Pirates of the Caribbean’ Premiere

Keira Knightley.Amanda Edwards/Getty

Amanda Edwards/Getty

Keira Knightlywas another star who wasn’t shy about flashing her midriff for the cameras.

At the 2003Pirates of the Caribbeanworld 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.

13of 13

Christina Aguilera.Evan Agostini/ImageDirect/Getty

Evan Agostini/ImageDirect/Getty

Christina Aguilerawas all over the denim trend in the early aughts.

Aguilera toldVoguein 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.”

source: people.com