How to Dress ’90s the Right Way in 2020

Clara Hendler/Backgrid, Getty Images

Throwback trends are always in and out of fashion, but one quick scroll through Instagram proves that learning how to dress ‘90s will score you major points in 2020—and won’t make you look like you were plucked straight out of a Delia’s catalog (RIP). Influencers and celebrities are sticking to the relaxed, sporty, and downright cool quality of the decade, which meshes remarkably well with mild temps of autumn and falls in line with quarantine’s effect on fashion as a whole.

Formfitting clothing has essentially flown out the window (save for a snug white tank top and bike shorts), and low-key ’90s style feels even more relevant during the strange times we’re living in.

Stylish ’90s kids like Emily Ratajwowski and Zoë Kravitz are keeping their childhood close to their closets and Instagram up-and-comers, like Gen Z fave Devon Carlson, are following suit. The list of ’90s-inspired trends seeing a revival is long, so we’re homing in on five trends that feel especially fresh for fall 2020. From utility pants to hair accessories and miniskirts you might wear for a Cher Horowitz Halloween costume, shop five looks that demonstrate how to dress ’90s like a pro.

1. Cargo pants

cargo pants illume
Aaliyah and RihannaGetty Images

You couldn’t watch the VMAs in the ’90s without spotting cargo pants. The roomy staple was a regular pick for pop stars like Aaliyah, TLC, and the Spice Girls. And now, when weekend outings consist of grocery store runs and mental health walks, the low-key pants are especially fitting. Plus, who doesn’t need some extra pocket room for added mask storage—or to ditch your bag altogether

2. Pleated skirts

pleated skirts illume
Claudia Schiffer and Zoë KravitzGetty Images, Backgrid

From Clueless to Empire Records, the pleated miniskirt was seen across the big screen in the ’90s, and now women are reworking the school-uniform staple in new ways. Whether you go grunge with Dr. Martens or make a nod toward tennis with trainers, the throwback skirt is bound to make an impact. Offset the leggy look with a chunky sweatshirt or a crop cardigan, à la Bella Hadid.

3. Bike shorts

bike shorts illume
Princess Diana and Hailey BaldwinBackgrid, Getty Images

Diana may have been Princess of Wales, but there’s no denying she was queen of the bike-shorts trend. The royal usually styled hers with an oversize sweatshirt and high socks and sneakers, coining an outfit formula that reads surprisingly chic—and has managed to take over Instagram two decades later. Modern-day trendsetters pair the shorts with boxy blazers for a flexible look with visible boss vibes, the ideal outfit combo for a time when we really do do it all.

4. Oversize blazers


oversize blazers illume
Julia Roberts and Katie HolmesGetty Images, @katieholmes

Style icons like Whitney Houston, Julia Roberts, and Winona Ryder all dabbled in statement suiting in the ’90s, and the oversize blazer has become an anchor for everyday outfits today. It instantly adds structure and grabs your attention without “doing too much,” and pairs well with slip dresses, athleisure, and vintage denim. Don’t be afraid to invest in a quality blazer—the piece isn’t going anywhere any time soon, and it’s a solid addition to your Zoom meeting apparel.

5. Claw clips

claw clips illume
Jennifer Love Hewitt and Bella HadidGetty Images

There’s no doubt that the ’90s were chock-full of questionable hairstyles. From Justin Timberlake’s signature “ramen noodle curls” to more butterfly clips than any one head of hair ever deserved, many are better left in the past—but claw clips are a pleasant resurgence that anyone can get behind. Kendall Jenner and Bella Hadid have added the accessory to their low-key beauty routines, often accented with gold hoops and face-framing tendrils you likely wore to prom way back when. Check out designer styles that could last a lifetime if handled with care, or opt for an affordable option if you know you’re bound to misplace it eventually.


Must Read