Aug 23, 2018

This Is What Cool Girls Were Wearing in Autumn 20 Years Ago

by Allyson Payer

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.

Julia Roberts, September 28, 1998

Photo:

Ron Galella, Ltd./WireImage

Can we please have this entire 'fit, Julia?

Jennifer Aniston, November 2, 1998

Photo:

Ron Galella, Ltd./Wireimage

These boots are perfection.

Tyra Banks and Cameron Diaz, October 21, 1998

Photo:

Ron Galella/WireImage

Meghan Markle would approve of their sheath dresses.

Keri Russell, November 4, 1998

Photo:

Ron Galella, Ltd./WireImage

The flip-flops somehow just work.

Charlize Theron, September 10, 1998

Photo:

Jeff Kravitz/FilmMagic, Inc

The most polished matching set.

Kate Moss, September 17, 1998

Photo:

Mazur/WireImage

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

Claudia Schiffer, October 29, 1998

Photo:

Steve Azzara/Corbis via Getty Images

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

Gabrielle Union, September 15, 1998

Photo:

Ron Galella, Ltd./WireImage

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

Chloë Sevigny, October 13, 1998

Photo:

Ron Galella/WireImage

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

Naomi Campbell, November 2, 1998

Photo:

Ron Galella, Ltd./WireImage

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

Winona Ryder, December 3, 1998

Photo:

Ron Galella, Ltd./WireImage

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

Cindy Crawford, October 19, 1998

Photo:

Ron Galella, Ltd./WireImage

'90s Cindy Crawford is such airport goals.

Jennifer Lopez, November 29, 1998

Photo:

Ron Galella, Ltd./WireImage

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

Gwyneth Paltrow, September 15, 1998

Photo:

Ron Galella, Ltd./WireImage

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

Angelina Jolie, December 10, 1998

Photo:

Frank Trapper/Corbis via Getty Images

Angelina Jolie would 100% wear this minimalist look today.

Mariah Carey, November 17, 1998

Photo:

Jim Spellman/WireImage

Yes, those are leather pedal pushers you see.

Nicole Kidman, November 17, 1998

Photo:

Arnaldo Magnani/Liaison/Getty Images

Nicole Kidman wears the tailoring look well.

Sarah Jessica Parker, September 21, 1998

Photo:

Ron Galella/WireImage

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

Shop Pieces Inspired by Fall 1998