The 1990s have influenced modern fashion in a major way. An era praised for effortlessly chic aesthetics, the decade gave birth to some of the most memorable style moments in sartorial history, while simultaneously cementing the icon status of key names in the industry: Naomi Campbell, Mary-Kate and Ashley Olsen, and Sarah Jessica Parker are all ’90s fashion icons we look to for styling tips today. Now, with new and legacy brands alike opting for a less-fussy approach to ’90s fashion—think: Michael Kors, Puppets and Puppets, Maisie Wilen, and Bevza—it’s as good a time as ever to re-create some of the most iconic celebrity looks from the era.
From chunky loafers that boosts anyone’s height (Simon Miller, Bottega Veneta) to minimal staples that can be mixed and matched with ease (The Row, Kiki de Montparnasse) it’s clear that the ’90s never left designers’ mood boards. Proenza Schouler’s collared cardigan set is reminiscent of Gwyneth Paltrow’s collared cardigan from the set of Great Expectations, and the sheer volume of cut-on-the-bias slipdresses available will bring back memories of Tom Ford–era Gucci throughout the iconic decade.
And then there’s Princess Diana’s off-duty style, which inspired many a designer to consider a more practical approach. Investing in an oversized puffer coat or a pair of bold biker shorts inspired by the princess is a no-brainer this season. Regardless of your personal style, there are looks worth bookmarking for inspiration before doing your fall shopping. Ahead, the most iconic ’90s fashion moments to recreate now.
The supermodel’s well-tailored leather skirt suit—an example of the hold menswear trends had on us in the ’90s—is a timeless classic that will work well in every wardrobe for seasons to come.
If you’re looking for pieces to help transition you through the seasons, you can’t go wrong with a summer knit similar to the one the actor wore on the set of Great Expectations. (Bonus points if it comes in a coordinating set, one of the biggest ’90s trends to make a comeback of late.)
Take a page out of supermodel Elle Macpherson’s book and swap your traditional trench for a posh navy-colored style. Not only is the reflective fabric a ’90s-specific trend, but it goes with everything.
Elizabeth Hurley’s airport look back in 1997 is nothing if not fall outfit inspiration. Plus, pay attention to the hem of her bootcut jeans—another present-day trend we stole from the ’90s.
Jada Pinkett Smith knows how to wear a suit. Seen here at the Men in Black premiere, she opted for a low-cut style with nothing underneath.
Sarah Jessica Parker, 1999
No stranger to a memorable fashion moment, SJP’s midi skirt is on par with styles on the market today. Dress yours up for fall with a pair of knee-high boots for a modern take on the ’90s skirtsuit.
Winona Ryder’s leather jacket—forever a wardrobe staple—is the perfect fall layering piece.
Very few do airport style quite like Grace Jones, so if you’re looking for a cozy look ahead of your next flight, opt for a (faux) fur coat layered over a hoodie with a super-chic hat.
Naomi Campbell, Claudia Schiffer, and Elle Macpherson, 1995
Three models, three iconic looks that we’d very much still wear today. (We’re pretty sure Claudia Schiffer’s skirt-and-knee-high-boots outfit just walked more than a few SS23 runways.)
It’s possible that Angela Bassett, seen here at the 1998 premiere of How Stella Got Her Groove Back, didn’t have any idea how many times this cut-on-the-bias gown would be referenced on runways years later.
Jennifer Aniston’s pinstriped suit is a true closet must-have. Give it a 2020 update by pairing it with bolder prints, à la the Friends star.
Halle Berry—at the fourth annual Blockbuster Awards, no less!—is iconic. The silk dress is an absolute must-have, and the sheer lace overlay is just the icing on the cake.
Model Iman demonstrates the power of the slipdress-oversized blazer combination.
One of her most iconic looks, Jennifer Lopez’s monochromatic outfit with low-rise jeans would work just as well today as it did in ’98.
A look that’s been re-created several times over the years, Princess Diana’s biker short ensemble is a foolproof way to be sporty chic.
Take a page out of Kate Moss’s book and mix textures for an all-black look that’s visually appealing too.
The silk slipdress, the round-toe Mary Janes, the dark sunglasses: Naomi Campbell’s nightclub look is quintessential ’90s.
Carolyn Bessette-Kennedy, 1996
Carolyn Bessette-Kennedy was a true style icon, so it makes sense that just about anything she wears would stand the test of time. This midi skirt-and-sweater combo is sure to be your go-to during winter months.
Is it Miu Miu spring/summer 2023, or is it Elle Macpherson in 1995? Who can say.
It’s nearly impossible to talk about ’90s style without mentioning Cindy Crawford—both on and off the catwalk. Invest in a suede coat to complete her effortless off-duty look.
Model Linda Evangelista is wearing a modern-day fall staple: a cropped tuxedo jacket. Style yours with high-waisted trousers or a skirt.
Everything about 1998-era Claire Danes is fall layering perfection, right down to the square-toe boots.
For those looking for a more daring approach, consider re-creating Claudia Schiffer’s vinyl-pant look from the ’90s. Adding a jumper or blazer gives the otherwise-trendy material a classic feel.
Mary-Kate and Ashley Olsen, 1999
The Olsen twins were just a mere 13 years old at the Anna and the King premiere in Los Angeles, but their matching midi skirt outfits—complete with beaded fridge at the hem—will go down in history as one of their best looks. (Paco Rabanne makes a great 2022 version.)
Jada Pinkett Smith further proves that a maxi skirt paired with a leather blazer will always be a chic option for a night out.
Okay, this look from Chanel’s spring/summer 1995 show might not showcase Claudia Schiffer’s personal style, but we know a gaggle of models who would wear this exact look right now—especially the belly chain.
The singer and entertainer made a strong case for the baseball cap trend by using a color-coordinated iteration to top off her relaxed tailoring look.
Cameron Diaz elevated her minimal skirt-and-sweater look with a beaded bag similar to styles that have gone viral on Instagram more than 30 years later.
Halle Berry’s demonstrating the power of the mom jean—the first time around. (The oval sunglasses and boxy bag are just the icing on the cake.)
Naomi Campbell’s lingerie-inspired look included a wine-colored slipdress layered under a shearling coat, making it a perfect ensemble for the cooler months.
If you told us Bella Hadid had this exact photo pinned on her inspiration board, we’d have no choice but to believe you.
The late singer brought major ’90s vibes with low-rise jeans, a thick-chain belt, and a crop top—a look that feels right at home today.
Again, not exactly a street style moment, but Paco Rabanne’s 1997 spring/summer collection feels suspiciously 2022, too.
The ’90s grunge queen’s combination of wide-leg, cuffed pants, and lug-sole boots feel very modern-day Marc Jacobs.
Gwyneth Paltrow’s one-step outfit marries comfort and style with ease, which is especially important when it comes to working remotely.
Cindy Crawford’s 1995 MTV Movie Awards look is giving present-day Jacquemus vibes.
What’s the over-under on some version of this look being in stock at Lisa Says Gah right now?
Jennifer Aniston’s open-knit sweater is perfect for the cooler months when the weather may be unpredictable.
Let Christy Turlington circa 1993 show you how to color-block for fall.
The queen of off-duty style, Princess Diana’s oversized puffer coat is the quality investment piece every wardrobe needs, and it’s sure to stand the test of time. Recreate the look with Aritzia’s Super Puff.
Jennifer Lopez’s beaded slipdress at the 17th annual CFDA Awards is ’90s—and present-day—perfection.
While Brooke Shields’s overall look has a vintage feel, the orange-colored lenses of her sunglasses really seal the deal. Lexxola’s Jordy Sunglasses are a great 2022 iteration of the trend.
With the resurgence of animal print, Mary J. Blige’s cheetah look at the 1996 Grammys—styled by Misa Hylton—could just as easily be worn in 2021.
Lauryn Hill’s faux-fur-lined coat is the star of this fit, but can we take a moment for her square-toe boots too?
Linda Evangelista’s off-duty look consisted of an easy outfit formula that’s worth re-creating: a mock turtleneck, boot-cut tailoring, and luxe accessories. It’s a guaranteed home run every time.
The former model-turned-actor put an elevated spin on pedal-pushers by pairing a fitted tank with barely-there sandals—quintessential ’90s style. (You may recognize the ’90s trend from one of Bella Hadid’s recent Instagrams.)
Planning to work from home this winter? Trade in your classic blazer for a “coatigan” (coat cardigan) to ensure a look that’s presentable and cozy.
A dead ringer for the style that Jennifer Lopez wore on the red carpet decades prior, Are You Ami’s Saia Tee is the plain white tee you never knew you needed.
Debra Messing’s full snake-print look may have a distinctly 2022 feel, but it was made popular in the ’90s. Opt for the trench coat only, if you’re not ready to take the plunge.
The supermodel’s choker-detail dress from the ’90s is just as chic now as it was then. Opting for a modern silhouette gives the style a fresh feel.
Shelby Ying Hyde
Shelby Ying Hyde is a Brooklyn-based shopping and fashion contributor BAZAAR.com, with bylines on The Zoe Report, Teen Vogue, Essence, Nylon, Elite Daily and more.
Lauren Caruso
Lauren Caruso is a freelance writer, consultant, and digital media strategist that splits her time between NYC and Los Angeles.
