This Is What Cool Girls Were Wearing in the Fall 20 Years Ago

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 XS to XL.
Available in sizes 0 to 12.
Next up, here are 10 celebrities in the '90s who we bet you won't recognize.

Allyson is a senior editor forBest Knockoff Luxury Clothing . She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories forBest Knockoff Luxury Clothing . Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a Stylist
Nice taste.
-
The '90s Dress-and-Shoe Pairing It Girls Are Wearing to Parties in East Hampton (Sorry, Flip-Flops, You Weren't Invited)
Classic elegance spotted at Gucci's star-studded soirée on Long Island.
-
Put Down the Black and White Pants—This Is the Richer Color You Didn't Know You Needed
Elegant and on-trend.
-
What You Should and Should Not Wear to Every Major Sporting Event
From a Liberty game to the French Open.
-
10 Outfits Europe's Chicest Dressers Are Wearing When They're *Not* on Vacation
Staying local is cool.
-
Just to Be Clear, *These* Are the Pants Fashion People in L.A. Are Wearing Instead of Basic Jeans
Spotted in Paris too.
-
The Coolest Outfits of Summer 2025 Are Actually the Laziest—Let Me Explain
Easy does it.
-
I Just Created 5 Incredibly Chic Summer Outfits From Amazon for Under $190
Cool looks for less.