These Are the Best Celebrity Winter Outfits from the '90s

In my (admittedly biased) opinion, ’90s style is the best. The looks from the decade I grew up in still influence how I get dressed to this day. Rooted in everything from minimal designs and larger-than-life silhouettes, ’90s style feels just as relevant today as it was decades ago. And as someone who needs fresh winter styling ideas, I regularly comb through ’90s street style snaps.

So what did celebrity winter outfits really look like over 20 years ago? Ahead, I’m highlighting some of the very best winter looks from the ’90s that would still look just as stylish today. From Halle Berry in monochrome to Cindy Crawford in a leather blazer to Jennifer Lopez in an iconic airport look, these are the celeb ’90s outfits you’ll want to repeat immediately.

Cindy Crawford demonstrating just how timeless a leather blazer is.

Same goes for Julia Roberts.

It doesn’t get more ’90s than Halle Berry’s sleek trench, striped pants, and oval sunglasses.

If you’re looking for the coolest way to dress for NYC in the winter, look no further than Carolyn Bessette Kennedy’s iconic outfits.

Gwyneth Paltrow’s cream satin trench is at the top of my wish list.

Pairing a charcoal jersey tee and skirt couldn’t be more simple or more chic. Thanks for the outfit inspiration, Jennifer Aniston.

Puffer coats are certainly back, but you’ll want to look to Princess Diana’s outfit for the coolest way to style one.

Cameron Diaz was wearing the double-sweater trend long before it was popular this winter.

When in doubt, layer a coat on top of a blazer like Lisa Bonet.

Make like Lucy Liu and wear a long coat with a faux-fur collar.

A pair of sheer tights are the ultimate way to make an outfit feel winter-ready.

Jennifer Lopez pulling off the perfect airport look with a tonal look in a white turtleneck and jeans.

Sharon Stone’s oversize nylon coat and sleek boots still feel so relevant for today.

This outfit alone is inspiring me to buy a pair of sheer brown tights and a sweaterdress.

A tee layered under a slip dress is one of the ultimate ’90s styling tricks. Just add a pair of boots and a faux-fur coat like Linda Evangelista did here to make it winter-ready.

Charlize Theron giving a classic pair of leather pants and button-down top a spin.

More leather-pant outfit ideas, this time from Reese Witherspoon.

Elizabeth Hurley wearing head-to-toe black to perfection.

Pajama dressing was practically born in the ’90s with looks like Alicia Silverstone’s.

Satin pants paired with Adidas sneakers? Yep, Kate Moss proving just how cool the pairing is.

If you’re stumped for stylish ways to pull off leggings, just look to Carla Bruni's chic outfit here for inspiration.

Next, discover the 25 best beauty products I tried this year.

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