It's hard to believe that 1998 was 20 years ago, but it was, and it happened to be a very stylish year. It was a year when the It girls at the time included Cameron Diaz, Kate Moss, Sarah Jessica Parker, and Keri Russell, and the It trends at the time included square-toed shoes, animal print, and slip skirts. (Sounds very 2018, don't you think?)
Just as we recently did for summer '90s outfits, we've left no '90s-fall-outfit stone unturned, and our look back at what cool girls were wearing in late 1998 has proven to be very fruitful. (Most intriguing to us is that celebrities hardly ever wore sneakers out, but they loved all-black outfits.) So if you adore '90s style, these looks will have you craving fall weather so that you can get into all the sweater sets, straight-leg jeans, and leather your heart desires.
Scroll on for 19 fall outfits that celebs wore 20 years ago (just be sure you scroll all the way down to SJP…), and shop pieces inspired by their looks.
Can we please have this entire 'fit, Julia?
These boots are perfection.
Meghan Markle would approve of their sheath dresses.
The flip-flops somehow just work.
The most polished matching set.
This may have something to do with the return of the strapless trend.
And this might have something to do with the return of the tiger-print trend.
A fitted sweater over a midi-length dress was a go-to look in 1998.
In case you wanted any more proof that trench coats are a classic…
Naomi Campbell's off-duty style has always been so chic.
Can't say we wouldn't wear that coat.
'90s Cindy Crawford is such airport goals.
If Jennifer Lopez still flew commercial, we wouldn't be surprised to see her wearing this.
We've never met a '90s Gwyneth Paltrow look we didn't love.
Angelina Jolie would 100% wear this minimalist look today.
Yes, those are leather pedal pushers you see.
Nicole Kidman wears the tailoring look well.
Yep, this is what SJP was wearing circa season 1 of Sex and the City.
Shop Pieces Inspired by Fall 1998
Available in sizes XXS to XL.
Available in sizes XS to XL.
Available in sizes XS to L.
Available in sizes 0 to 12.
Available in sizes XXS to XL.
Available in sizes 0 to 10.
Available in sizes 16 to 30.
Available in sizes 24 to 31.
Next up, here are 10 celebrities in the '90s who we bet you won't recognize.
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Goodbye, Bubble Shorts—Everyone Everywhere Is Wearing This "Dated" Pant Trend InsteadHere's how It girls in New York, London, Copenhagen, and more are styling them in 2025.
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Dua Lipa and Miley Cyrus Traded In Their Dark-Wash Denim for This '90s ThrowbackHalle Berry and Cindy Crawford also approve.
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Cooler Than Jeans and a T-Shirt—Everyone With Good Taste Will Wear These 15 Denim Outfits This FallNext time fall styling inspiration runs dry, just reference these looks.
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Goodbye, Ballet Flats: It Girls in London, NYC, and Paris Are Prioritizing This Fall Flat Shoe Trend InsteadAnd they're styling it like *this.*
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Every Fall Outfit I Want to Wear This Year (So Far)These looks are the definition of effortless.
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Everyone Is Suddenly Wearing This Expensive-Looking Item With White PantsSo chic.
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No One Wears a White T-Shirt Quite Like a Fashion Person—6 Incredibly Cool Looks to Re-Create NowNothing but chic, effortless vibes.
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The French-Girl Way to Style Black Capris This FallOutfit inspiration inside.
