50 Iconic Outfits from the ’90s to Re-create Today (2024)

From chunky loafers that boosts anyone's height (Simon Miller, Bottega Veneta) to minimal staples that can be mixed and matched with ease (The Row, Kiki de Montparnasse) it's clear that the '90s never left designers' mood boards. Proenza Schouler's collared cardigan set is reminiscent of Gwyneth Paltrow's collared cardigan from the set of Great Expectations, and the sheer volume of cut-on-the-bias slipdresses available will bring back memories of Tom Ford–era Gucci throughout the iconic decade.

And then there's Princess Diana's off-duty style, which inspired many a designer to consider a more practical approach. Investing in an oversized puffer coat or a pair of bold biker shorts inspired by the princess is a no-brainer this season. Regardless of your personal style, there are looks worth bookmarking for inspiration before doing your fall shopping. Ahead, the most iconic '90s fashion moments to recreate now.

The supermodel's well-tailored leather skirt suit—an example of the hold menswear trends had on us in the '90s—is a timeless classic that will work well in every wardrobe for seasons to come.

If you're looking for pieces to help transition you through the seasons, you can't go wrong with a summer knit similar to the one the actor wore on the set of Great Expectations. (Bonus points if it comes in a coordinating set, one of the biggest '90s trends to make a comeback of late.)

Take a page out of supermodel Elle Macpherson's book and swap your traditional trench for a posh navy-colored style. Not only is the reflective fabric a '90s-specific trend, but it goes with everything.

Elizabeth Hurley's airport look back in 1997 is nothing if not fall outfit inspiration. Plus, pay attention to the hem of her bootcut jeans—another present-day trend we stole from the '90s.

Jada Pinkett Smith knows how to wear a suit. Seen here at the Men in Black premiere, she opted for a low-cut style with nothing underneath.

No stranger to a memorable fashion moment, SJP's midi skirt is on par with styles on the market today. Dress yours up for fall with a pair of knee-high boots for a modern take on the '90s skirtsuit.

Winona Ryder's leather jacket—forever a wardrobe staple—is the perfect fall layering piece.

Very few do airport style quite like Grace Jones, so if you're looking for a cozy look ahead of your next flight, opt for a (faux) fur coat layered over a hoodie with a super-chic hat.

Three models, three iconic looks that we'd very much still wear today. (We're pretty sure Claudia Schiffer's skirt-and-knee-high-boots outfit just walked more than a few SS23 runways.)

It's possible that Angela Bassett, seen here at the 1998 premiere of How Stella Got Her Groove Back, didn't have any idea how many times this cut-on-the-bias gown would be referenced on runways years later.

Jennifer Aniston's pinstriped suit is a true closet must-have. Give it a 2020 update by pairing it with bolder prints, à la the Friends star.

Halle Berry—at the fourth annual Blockbuster Awards, no less!—is iconic. The silk dress is an absolute must-have, and the sheer lace overlay is just the icing on the cake.

Model Iman demonstrates the power of the slipdress-oversized blazer combination.

One of her most iconic looks, Jennifer Lopez's monochromatic outfit with low-rise jeans would work just as well today as it did in '98.

A look that's been re-created several times over the years, Princess Diana's biker short ensemble is a foolproof way to be sporty chic.

Take a page out of Kate Moss's book and mix textures for an all-black look that's visually appealing too.

The silk slipdress, the round-toe Mary Janes, the dark sunglasses: Naomi Campbell's nightclub look is quintessential '90s.

Carolyn Bessette-Kennedy was a true style icon, so it makes sense that just about anything she wears would stand the test of time. This midi skirt-and-sweater combo is sure to be your go-to during winter months.

Is it Miu Miu spring/summer 2023, or is it Elle Macpherson in 1995? Who can say.

It's nearly impossible to talk about '90s style without mentioning Cindy Crawford—both on and off the catwalk. Invest in a suede coat to complete her effortless off-duty look.