The 1990s was a decade that had a lot going for it: the advent of the supermodel, grunge culture, Seinfeld, Tamagotchi pets, and fashion trends with a minimalist bent. But the '90s were also a 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 denim outfits featured 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 jeans have such staying power is in large part thanks to the individuals who made the look so memorable. Fashion icons of the era, such as Gwyneth Paltrow, Janet Jackson, and Princess Diana, have re-entered the zeitgeist as ‘90s trends return to popularity across the fashion spectrum. But why now?
Confident, authentic personal style is emblematic of the 1990s — at the time, an emphasis on comfort was key. Now, as people navigate the transition from cozy sweats toward trousers and blazers, they’re looking for fashion that bridges the gap. Unsurprisingly, relaxed denim blends in seamlessly with almost anything, which makes unearthing the best '90s-style jeans a lesson in dressing for today, too. Ahead, 18 standouts to inspire your own wardrobe.
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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.
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 artfully blends aesthetics with a beret and bodysuit up top, along with a Western belt and relaxed denim below. Sleek black boots add an elevated touch to slouchy jeans.
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.
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.
Twin Peaks star Joan Chen accessorizes a pared-down blue jeans look with a statement hat, pilgrim blouse, and vest. Add a waistcoat of your own, and try a baseball cap for a more modern vibe.
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.
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 or corset top.
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.
Actor, writer, director, and producer Justine Bateman exudes quiet coolness with this simple denim ensemble. To recreate her look, try a cropped jacket in suede, velvet, or silk.
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.
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 — and Brad Pitt by your side.
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.
Ally McBeal obsessions aside, this denim look from Calista Flockhart should be your next night-out look. A barely buttoned white blouse under a slick black jacket with a pair of low rise, lightly frayed jeans? Always cool and effortless.
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.
If you need a new layering combination, try a denim jacket tied around your waist with blue jeans and a contrast blouse. As seen on Patricia Arquette, the result is charming, cool, and very all-American.
What’s left to say? Kate Moss’s minimalist style is forever a favorite. To take mid-rise jeans and a fitted tank top up a notch, add a simple chain necklace and a pair of heeled sandals.
Supermodel Tyra Banks shows that a baseball cap and t-shirt are best when worn with classic blue jeans. This sporty sneakers look translates directly to 2022.
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