This Is What Cool Girls Were Wearing in Autumn 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-autumn-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 autumn weather so that you can get into all the sweater sets, straight-leg jeans, and leather your heart desires.

Scroll on for 19 autumn 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.

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Julia Roberts, September 28, 1998
(Image credit: Ron Galella, Ltd./WireImage)

Can we please have this entire 'fit, Julia?

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Jennifer Aniston, November 2, 1998
(Image credit: Ron Galella, Ltd./Wireimage)

These boots are perfection.

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Tyra Banks and Cameron Diaz, October 21, 1998
(Image credit: Ron Galella/WireImage)

Meghan Markle would approve of their sheath dresses.

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Keri Russell, November 4, 1998
(Image credit: Ron Galella, Ltd./WireImage)

The flip-flops somehow just work.

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Charlize Theron, September 10, 1998
(Image credit: Jeff Kravitz/FilmMagic, Inc)

The most polished matching set.

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Kate Moss, September 17, 1998
(Image credit: Mazur/WireImage)

This may have something to do with the return of the strapless trend.

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Claudia Schiffer, October 29, 1998
(Image credit: Steve Azzara/Corbis via Getty Images)

And this might have something to do with the return of the tiger-print trend.

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Gabrielle Union, September 15, 1998
(Image credit: Ron Galella, Ltd./WireImage)

A fitted sweater over a midi-length dress was a go-to look in 1998.

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Chloë Sevigny, October 13, 1998
(Image credit: Ron Galella/WireImage)

In case you wanted any more proof that trench coats are a classic…

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Naomi Campbell, November 2, 1998
(Image credit: Ron Galella, Ltd./WireImage)

Naomi Campbell's off-duty style has always been so chic.

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Winona Ryder, December 3, 1998
(Image credit: Ron Galella, Ltd./WireImage)

Can't say we wouldn't wear that coat.

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Cindy Crawford, October 19, 1998
(Image credit: Ron Galella, Ltd./WireImage)

'90s Cindy Crawford is such airport goals.

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Jennifer Lopez, November 29, 1998
(Image credit: Ron Galella, Ltd./WireImage)

If Jennifer Lopez still flew commercial, we wouldn't be surprised to see her wearing this.

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Gwyneth Paltrow, September 15, 1998
(Image credit: Ron Galella, Ltd./WireImage)

We've never met a '90s Gwyneth Paltrow look we didn't love. Those shoes are so 2018.

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Angelina Jolie, December 10, 1998
(Image credit: Frank Trapper/Corbis via Getty Images)

Angelina Jolie would 100% wear this minimalist look today.

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Mariah Carey, November 17, 1998
(Image credit: Jim Spellman/WireImage)

Yes, those are leather pedal pushers you see.

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Nicole Kidman, November 17, 1998
(Image credit: Arnaldo Magnani/Liaison/Getty Images)

Nicole Kidman wears the tailoring look well.

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Sarah Jessica Parker, September 21, 1998
(Image credit: Ron Galella/WireImage)

Yep, this is what SJP was wearing circa season 1 of Sex and the City

Shop Pieces Inspired by Fall 1998

Next up, here are 10 celebrities in the '90s who we bet you won't recognise.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. 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. 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.