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If you keep up with the latest trends (both off and on the runway), then you know that 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—like Naomi Campbell and Sarah Jessica Parker. Now, with your favorite designers opting for a less-fussy approach to 2020, it’s as good a time as ever to re-create some of those yesteryear celebrity looks.
From chunky footwear that boosts one’s height to minimal staples that can be mixed and matched with ease, it’s clear that the ’90s never left designers’ mood boards. Take Stella McCartney, whose sock-style platform boot is reminiscent of a similar (less bulky) boot worn by Carolyn Bessette-Kennedy—a true style icon of the time. Or emerging label Calle Del Mar. Known among the style set on Instagram for its fitted knitwear, the brand created one particular knit that resembles a top worn by Gwyneth Paltrow on the set of the classic ’90s film Great Expectations. And then there’s Princess Diana. The late royal’s viral off-duty style has 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 is a variety of looks worth bookmarking for inspiration before doing your fall shopping. Just ahead, the 26 best fashion moments from the ’90s and the key pieces you need to get the looks.
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Naomi Campbell, 1991
The supermodel’s well-tailored leather skirt suit circa 1991 is a timeless classic that will work well in every wardrobe for seasons to come.
Get the Look: LVIR Faux-Leather Jacket, $460, net-a-porter.com.
Gwyneth Paltrow, 1996
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 coordinate set.)
Get the Look: Calle Del Mar Ribbed-Knit Shirt, $350, net-a-porter.
Elle Macpherson, 1996
Take a page out of supermodel Elle Macpherson’s book and swap your traditional trench for a posh navy-colored style—it goes with everything.
Get the Look: Tagliatore Belted Midi Coat, $1,095, farfetch.com.
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.
Get the Look: Jacquemus Valerie Canvas Midi Skirt, $533, matchesfashion.com.
Grace Jones, 1990
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.
Get the Look: Stand Studio Theresa Faux Fur Coat, $325, matchesfashion.com.
Jennifer Aniston, 1998
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.
Get the Look: Monse Two-Tone Pinstripe Asymmetric Blazer, $1,790, farfetch.com.
Jennifer Lopez, 1998
One of her most iconic looks, Jennifer Lopez’s monochromatic outfit would work just as well today as it did in ’98.
Get the Look: Khaite Eda Bralette, $520, khaite.com.
Princess Diana, 1995
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.
Get the Look: Rielli Maldive Shorts, $60, riellibrand.com.
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.
Get the Look: Stella McCartney Sock-Style Platform Boots, $725, farfetch.com.
Cindy Crawford, 1994
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.
Get the Look: Theory Suede Single-Breasted Coat, $1,482, farfetch.com.
Claudia Schiffer, 1995
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.
Get the Look: Commando Faux Leather Leggings, $98, shopbop.com.
Jada Pinkett Smith, 1998
Jada Pinkett Smith further proves that a maxi skirt paired with a leather blazer will always be a chic option for a night out.
Get the Look: Uniform Person Lumi Long Skirt with Back Slit, $110, uniform-person.com.
Janet Jackson, 1994
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.
Get the Look: Cold Laundry CL Cap Shell Hat, $42, coldlaundrystores.com.
Cameron Diaz, 1998
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.
Get the Look: Shrimps Mini Antonia Bag, $585, shrimps.com.
Naomi Campbell, 1997
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.
Get the Look: Marques’Almeida Tie Side Silk Slipdress, $516, brownsfashion.com.
Gwyneth Paltrow, 1996
Gwyneth Paltrow’s one-step outfit marries comfort and style with ease, which is especially important when it comes to working remotely.
Get the Look: Song of Style Polly Midi Dress, $168, revolve.com.
Jennifer Aniston, 1995
Jennifer Aniston’s open-knit sweater is perfect for the cooler months when the weather may be unpredictable.
Get the Look: Dion Lee Open-Knit Detail Top, $490, farfetch.com.
Princess Diana, 1994
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.
Get the Look: Moncler Maire Quilted Down Puffer Jacket, $1,290, saksfifthavenue.com.
Brooke Shields, 1998
While Brooke Shields’s overall look has a vintage feel, the orange-colored lenses of her sunglasses really seal the deal.
Get the Look: Vehla Dixie Sunglasses, $180, vehlaeyewear.com.
Mary J. Blige, 1996
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 2020.
Get the Look: Mugler Cropped Leopard-Print Cotton-Blend Flared pants, $830, net-a-porter.com.
Linda Evangelista, 1995
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.
Get the Look: Pleats Please Issey Miyake Black Basic Sleeveless Turtleneck Top, $225, ssense.com.
Garcelle Beauvais, 1998
The former model-turned-actor put an elevated spin on pedal-pushers by pairing a fitted tank with barely there sandals—quintessential ’90s style.
Get the Look: Staud Mikayel Pants, $165, staud.clothing.
Uma Thurman, 1995
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.
Get the Look: Totême Grey Marled Wool Treviso Cardigan, $420, ssense.com.
Jennifer Lopez, 1999
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.
Get the Look: Are You Ami Saia Tee, $90, areyouami.com.
Debra Messing, 1999
Debra Messing’s full snake-print look may have a distinct 2020 feel, but it was made popular in the ’90s. Opt for the trench coat only, if you’re not ready to take the plunge.
Get the Look: Dries Van Noten Snake-Print Coated Cotton-Blend Trench Coat, $1,845, net-a-porter.com.
Kate Moss, 1995
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.
Get the Look: Bottega Veneta Cutout Knitted Turtleneck Dress, $2,360, net-a-porter.com.
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