(Style)

'90s Denim Throwbacks Never Get Old, Here Are 18 You Need to See

A walk down blue jean memory lane.

Ron Galella/Ron Galella Collection/Getty Images
Drew Barrymore wearing jeans in the '90s

The 1990s was a decade that had a lot going for it. The advent of the supermodel, punk culture, Seinfeld, Tamagotchi pets, and fashion trends with a minimal or grunge bent. But the '90s were also the golden age of denim. The relaxed fit was just right — a mid-rise, straight leg silhouette, with a light, worn wash (take a glance at the Calvin Klein ads of the time for a refresher). Looking back, many of the best '90s jeans outfits were men and women dressed in the still-iconic Levi's 501®, which is why it's so easy to recreate these outfits today (rather affordably, you might add).

Timeless design details and classic American brands aside, a big reason why '90s denim has such staying power is in large part thanks to the individuals who made it so memorable. Icons of fashion at the time like Gwyneth Paltrow and Janet Jackson have re-entered the zeitgeist as ‘90s trends return to popularity across the fashion spectrum. Why now? Confident, authentic personal style is emblematic of the era and for many, an emphasis on comfort was key. As many women navigate the transition from cozy sweats towards hard pants and blazers, they’re looking for fashion that bridges the gap. Unsurprisingly, relaxed denim blends in seamlessly with all of the above, which makes unearthing the best '90s blue jean throwbacks a lesson in dressing for today, too. Ahead, 18 standouts to inspire your own wardrobe.

Princess Diana

Tim Graham/Tim Graham Photo Library/Getty Images

Princess Diana’s personal style needs no introduction. This denim-on-denim number featuring a Western belt and cowboy boots is a look just waiting to be recreated. To break up high-waisted denim and a coordinated shirt, choose a wide, contrasting belt to cinch around your midsection.

Brooke Shields

Ron Galella, Ltd./Ron Galella Collection/Getty Images

There’s no combination easier to pull together than a t-shirt and blue jeans pairing. Top it off with a suede jacket and leather belt à la Brooke Shields and balance out more casual pieces with sleek loafers.

Janet Jackson

Ron Galella, Ltd./Ron Galella Collection/Getty Images

Janet Jackson artfully blends aesthetics with a beret and bodysuit up top, and a Western belt and relaxed denim below. Sleek black boots add an elevated touch to slouchy jeans.

Jennifer Aniston

Barry King/WireImage/Getty Images

Jennifer Aniston nails relatable, polished style with this sheen button-down shirt and blue jeans pairing. For a more modern take, try leaving your button-down untucked, with only the top few buttons done.

Jane Birkin

Laurent MAOUS/Gamma-Rapho/Getty Images

Always the style inspiration, Jane Birkin proves a simple blouse and blue jeans combination always feels fresh. While bell bottoms may be best known as the silhouette of the ‘70s, a relaxed flare with a high waist works for a ‘90s-inspired look, too.

Joan Chen

Ron Galella, Ltd./Ron Galella Collection/Getty Images

Twin Peaks star Joan Chen accessorizes a pared-down blue jeans look with a statement hat and vest. Add a waistcoat of your own, and try a classic baseball cap for a 2021 vibe.

Julia Roberts

Ron Galella, Ltd./Ron Galella Collection/Getty Images

For a denim-on-denim look with a Western twist, Julia Roberts accessorizes her Canadian tuxedo with a Concho belt and cowboy boots. Copy the look, but avoid any fringe or a wide-brim hat to keep the ensemble from skewing too costume-y.

‘90s Denim: Tori Spelling

Jeff Kravitz/FilmMagic, Inc/Getty Images

Beverly Hills, 90210 star Tori Spelling serves up ‘90s Hollywood style with a leather vest and blue jean pairing. For a cool take, try swapping out leather for an on-trend sweater vest.

Angela Bassett

Steve Granitz/WireImage/Getty Images

A waistcoat with jeans isn’t a new trend, as illustrated by the imitable Angela Bassett circa 1996. For denim that’s just a bit too long, consider cuffing your wide jeans just above the hem.

Justine Bateman

Michael Ochs Archives/Michael Ochs Archives/Getty Images

Actor, writer, director, and producer Justine Bateman exudes quiet coolness with this simple denim ensemble. To recreate her look, try a cropped jacket in velvet or silk.

Drew Barrymore

Ron Galella/Ron Galella Collection/Getty Images

Queen of the ‘90s, Drew Barrymore’s slightly sweet, slightly subversive take on blue denim is why we keep returning to her looks during this iconic decade. Grab your favorite cropped cardigan to re-do this look off the red carpet.

Gwyneth Paltrow and Brad Pitt

Frank Trapper/Corbis Entertainment/Getty Images

If you want an easy, polished take on ‘90s trends, try a leather blazer and relaxed-fit jeans like Gwyneth Paltrow. Finish with boots or a pair of mules.

Winona Ryder

Ron Galella, Ltd./Ron Galella Collection/Getty Images

A ‘90s denim roundup isn’t complete without a nod to Winona Ryder. This outfit will forever be in the blue jean hall of fame, solidifying the necessity of a fitted leather jacket and combat boots.

Calista Flockhart

Evan Agostini/Hulton Archive/Getty Images

Ally McBeal obsessions aside, this denim look from Calista Flockhart should be your next night-out look.

Halle Berry

Jeff Kravitz/FilmMagic, Inc/Getty Images

Halle Berry’s fringe vest and blue jeans prove that you can’t put ‘90s style in a box; it’s more about a feeling than a specific outfit combination. Today, a cutout crop top and colorful, chunky necklaces embodies the same vibe.

Patricia Arquette

Jeff Kravitz/FilmMagic, Inc/Getty Images

If you need a new layering combination, try a denim jacket tied around your waist with blue jeans below. As seen on Patricia Arquette, the result is charming and cool.

Kate Moss

Michael Ochs Archives/Michael Ochs Archives/Getty Images

What’s left to say? Kate Moss’s minimalist style is forever a favorite. To take jeans and a fitted tank top up a notch, add a simple chain necklace and a pair of heeled sandals.

Tyra Banks

Jeff Kravitz/FilmMagic, Inc/Getty Images

Supermodel Tyra Banks shows that a baseball cap and tee are best when worn with classic blue jeans. This sporty sneakers look translates directly to 2021.