3 Words: '90s Fall Outfits

I don’t know about you, but the last thing I care about right now is summer style when I know that the time for fall fashion is less than one month away. You could have already guessed that based on some of my recent articles, such as this one about my favorite boot trends, this one about the style mistakes I make every fall and how I plan to fix them, and this one about the trend that has me putting a pause on jeans. But I figured I should say it (again) anyway. After all, it really is the most stylish season of the year and, as always, the inspiration is abundant.

Since I’ve already shown you the more modern outfits I’ll be sporting in the months to come, I figured why not take it back a couple decades and draw some inspiration from our favorite ‘90s style icons. From Carolyn Bessette-Kennedy to Naomi Campbell, ahead you’ll find 11 outfits from 1990 to 1999 that somehow feel unbelievably fresh for 2019. See (and shop) them below.

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Halle Berry, 1994
(Image credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images)

Pretty much every aspect of Halle Berry's outfit is back in style today: leopard print, lace-up boots, vintage-inspired jeans, and structural bags.

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Gwyneth Paltrow, 1996
(Image credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images)

If you're all about minimalism, look no further than Gwyneth Paltrow's sleek head-to-toe black look (and be sure to note her on-trend boots). 

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Sarah Jessica Parker, 1997
(Image credit: Richard Corkery/NY Daily News Archive via Getty Images)

Proof that statement coats and slingbacks were as essential then as they are now.

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Jennifer Lopez, 1999
(Image credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images)

I'll be emulating this exact color scheme in my sweater-and-jean outfits this fall.

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Iman, 1991
(Image credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images)

Iman's all-black and leather outfit is definitely something you'd see on the runway today. Also, how chic does she make leggings look?

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Julia Roberts, 1991
(Image credit: The LIFE Picture Collection via Getty Images)

Leave it to '90s Julia Roberts to demonstrate the timelessness of a blazer, tee, and jeans.

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Naomi Campbell, 1990
(Image credit: The LIFE Picture Collection via Getty Images)

Nineties Naomi is the epitome of class in this tweed jacket and slip skirt.

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Victoria Beckham, 1997
(Image credit: Dave Benett/Getty Images)

Before her fashion empire, Posh Spice was already known for her many little black dresses.

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Carolyn Bessette-Kennedy, 1999
(Image credit: Evan Agostini/Getty Images)

Have a party to go to this fall? Take a break from dresses and try Carolyn Bessette-Kennedy's look: a button-down and skirt.

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Tyra Banks, 1997
(Image credit: Marion Curtis/DMI/The LIFE Picture Collection via Getty Images)

Tyra Banks is making me realize I have to add more cardigans and strappy sandals to my shopping cart.

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Cindy Crawford, 1990
(Image credit: Ron Galella/Ron Galella Collection via Getty Images)

Cindy (and now Kaia) has rocked many a leather blazer in her time, and this is just one of the many memorable outfits.

Up next? 18 items that will be in every style snap next month.

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Editor-at-Large

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. It was a less expected route, seeing as she was graduating from business school at USC when this all began, but it has turned out to be the best one for her. Fast-forward to 2024, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was an intern starting out. Currently, she focuses on a weekly mélange of shopping content. As far as her personal style goes, she's largely drawn to classic pieces and neutral basics but will always make an exception for something colorful, printed, or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a good party is dressing up for one. On weekdays, she can usually be found at home eating something delicious for dinner and trying to force her husband to watch Summer House.