'90s Jeans Outfits That Are Iconic Enough To Recreate Today

A walk down blue jean memory lane.

Originally Published: 
Cher in jeans in 1991

The 1990s was a decade that had a lot going for it: the advent of the supermodel, grunge culture, Sex and the City, Tamagotchi pets, and fashion trends with a minimalist bent. It was also a golden age of denim. The relaxed fit of the era 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 featured the still-iconic Levi’s 501, which is why it’s so easy to recreate these looks today (rather affordably, you might add). Further, modern day brands, such as AGOLDE, RE/DONE, and Mother Denim, have taken note of Levi’s decades of success and implemented their own variations of classic denim styles into their offerings.

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 — think Drew Barrymore, Naomi Campbell, and Cher — 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, outfits that felt effortless and comfortable were the ones that made waves. Now, as people are navigating the balance between easy-to-wear garments and on-trend styles, they’re looking for outfit inspiration that feels put together without compromising on functionality. Unsurprisingly, relaxed denim blends in seamlessly with almost anything, from blazers to graphic T-shirts, which makes unearthing the best ‘90s-style jeans a lesson in dressing for today, too. Ahead, check out the standout outfits from your favorite ‘90s stars that’ll help to inspire your own wardrobe.

Cindy Crawford

Ron Galella, Ltd./Ron Galella Collectio

The supermodel is notorious for wearing effortlessly cool ensembles to the airport and this look from 1997 confirms she’s been nailing the travel wardrobe for decades. To create an outfit that’s both comfortable and put together, use Crawford’s formula by styling a pair of jeans with a neutral T-shirt and a leather blazer.


Ron Galella/Ron Galella Collection

If you want to give your jeans a subtle flair, opt for patch designs like Cher did with this star-studded ensemble. Because of the pant’s bold detail, keep the rest of the look classic with a loose-fitting leather jacket and coordinating black belt.

Naomi Campbell

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Instead of reaching for a plain white tee, get an off-duty model look by reaching for a graphic option instead. This will give your outfit a bit more personality while retaining a minimalist feel.

Meryl Streep

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While denim isn’t traditional for a red carpet, Streep was never afraid to break the rules. She dressed up her pair by styling it with pointed-toe boots and an oversized blazer. Make the ensemble feel luxe by adding in a pair of gold hoops.

Sarah Jessica Parker

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Whether you’re playing or just cheering from the sidelines, Parker’s rolled up, low-rise denim look feels playful and functional for active days ahead. Make the outfit work from the field to date night by opting for a graphic T-shirt instead of a cropped tank top.

Jane Fonda

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If your style leans more sporty, go with Fonda’s formula by styling a short-sleeve button-down with a pair of jeans. While Fonda tucked her top in, leave it loose for a look that feels a bit more contemporary. For the sunny days, throw on your favorite baseball cap to add functionality to the outfit.

Victoria Beckham

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Posh Spice was beloved for her sultry style in the ‘90s and this going-out ensemble exemplifies the party vibe she favored. Instead of wearing light wash denim, she opted for a darker hue. Mix it with a sparkly top (preferably with cutouts) to get a look designed for the dance floor.

Whitney Houston

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While the singer’s look comes from 1994, this outfit feels totally relevant right now. It features all the fashionista must-haves: a white button-down, an oversized blazer, and a pair of straight leg jeans. To give the minimalistic look some edge, try topping your own version off with a creamy bucket hat — your summer wardrobe will thank you.

Drew Barrymore

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Queen of the ‘90s (and every decade, really) Drew Barrymore put a slightly sweet, slightly subversive take on blue denim that’s well worth a revisit. Grab your favorite cropped cardigan to recreate this effect off the red carpet.

Uma Thurman

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If you reside somewhere prone to frigid temperatures, the easiest way to spice up a simple jean outfit is with a bright colored trench coat. Thurman opted for a bold red color, which still works for now.

Jennifer Aniston

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Jennifer Aniston nailed relatable, polished style with a sheer button-down shirt and blue jeans pairing. For a 2022 take, try leaving your button-down untucked, with only the top few buttons clasped.

Mariah Carey

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To give your denim collection an edgy twist, opt for a raw hem style. You can find more subtle pairs with purposefully unfinished edges on the bottom or emulate Carey by looking for the detail at the waist.

Demi Moore

Ron Galella, Ltd./Ron Galella Collection

The actor put a fresh spin on the classic blazer and denim combination by wearing a striped tank top underneath. It’s just the idea to shake things up if you’re tired of styling a classic white T-shirt underneath your blazer.

Princess Diana

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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.

Brooke Shields

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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 the casual pieces with sleek loafers.

Janet Jackson

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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 the slouchy jeans.

Jane Birkin

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A forever style inspiration, Birkin proves a simple blouse and blue jeans combination is timeless. 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

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Twin Peaks star Joan Chen accessorized 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.

Julia Roberts

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For a Canadian tuxedo with a Western twist, Roberts accessorizes 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.

Tori Spelling

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Beverly Hills, 90210 star Spelling served up ‘90s Hollywood style with a leather vest and blue jean pairing. For a right-now update, try swapping out leather for an on-trend sweater vest or corset top.

Angela Bassett

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

Justine Bateman

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

Gwyneth Paltrow

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

Winona Ryder

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No ‘90s denim roundup is complete without a nod to the now Stranger Things actor. 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

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Ally McBeal obsessions aside, aren’t you obsessed with this denim look? Like, a barely buttoned white blouse under a slick black jacket with a pair of low rise, lightly frayed jeans? It’s always cool and effortless.

Halle Berry

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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

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If you need a new layering combination, try a denim jacket tied around your waist with blue jeans and a contrasting blouse. As seen on Arquette, the result is charming, cool, and very all-American.

Kate Moss

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What’s left to say? Moss’ minimalist style always sticks the landing. To take mid-rise jeans and a fitted tank top up a notch, add a simple chain necklace and a pair of heeled sandals.

Tyra Banks

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The supermodel 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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