How To Wear '90s Trends The RIGHT Way

Update: This post was originally published on Jun 30, 2015.

When the whole '90s-revival thing picked up steam most recently, I didn’t think twice about whipping out my overalls and buying a new tattoo choker on Etsy. No shame there — I’m a '90s kid, after all. But I'll admit that the return of these trends can look either amazing...or just really, really bad.

We’ve watched our favorite '90s stars’ and fashion icons’ styles evolve over the years, but there’s still something magical (and hilarious) about remembering the big hits of the decade — like the Rachel haircut or Cher Horowitz’s epic outfits in Clueless. Pieces like overalls and crop tops can certainly take more modern, streamlined forms nowadays, but still, mastering their return is all about styling. There's a fine line between giving a chic nod to the '90s and looking like a character from Spice World.

To help you avoid going into full-on time-capsule mode, we put together outfits that tap into the '90s the right way. So go on, learn how to bring these signatures back to the future.

The Choker, Then
Talk about a throwback. Christina Aguilera's choker is just the finishing touch on her quintessential '90s look. The super-low-rise pants, the baby tee with intentionally layered cami underneath, the micro-eyebrows, and a dose of attitude are giving us major flashbacks.

Aside from tattoo chokers, black bands with a single charm were everywhere (mine had a yin-yang charm, obviously). Oh, and if you didn't feel like spending money on one, you could always cut off a ring of fabric from a pair of black tights and just wear that around your neck. Let's not relive that look.
The Choker, Now
Think of your choker as a sleek accessory to tie together an office-appropriate look in a fresh way, rather than a front-and-center piece. Forgo a pendant for a minimal metal version, and layer it with your simple, wear-every-day chain necklaces for added interest. Wear it with a flowy top, a bold pair of tailored trousers, and a bit of a heel, and you’re honing in on the trend without going full-on '90s pop star.

Lizzie Fortunato Silver Wave Double Choker, $380 $275, available at Lizzie Fortunato.
Tibi Plaid Shirting, $395, available at Tibi.
Rachel Comey Factor Earrings Tortoise, $115, available at Beklina.
ASOS Hold On Leather Heeled Sandals, $87, available at ASOS.
Photo: Jeff Kravitz/Getty Images.
The Crop Top, Then
Tyra, you babe. She went full-on with mom jeans, bright white sneakers, a metallic backpack, and a backwards hat. She pulled it off, no doubt, but this look might not fly today, especially at the office. The good thing about the return of the crop top, though, is that the possibilities are endless (and don't require maximum tummy exposure).
The Crop Top, Now
You don't have to convince us to love a crop top — at this point, they've become a staple in our wardrobes. But there's always a chance of looking a little too '90s, especially if you fall into wearing one with boyfriend jeans and a flannel tied around your waist. Instead, opt for a ladylike, knee-length skirt and a studded shoe with a bit of a heel. The classic black bag makes the outfit look all grown up, while a whimsical statement ring keeps it playful.

Cienne The Sonya Top, $395, available at Spring.
Modern Weaving Brass Moon Dancer Earrings, $120, available at Ban.do.
Topshop Joyous Mid Heel, $85, available at Topshop.
Charles and Keith Curved Boxy Sling Bag $59, available at Charles and Keith.
Photo: ABC Photo Archives/Getty Images.
The Overalls, Then
We'll just leave this here... In all seriousness, what would the decade have been without overalls? They were fun to wear as a kid, no doubt, and made an appearance in just about every Mary-Kate and Ashley movie, so obviously they were a must-have — especially when paired with a straight-up soccer-mom haircut. Sure, they were probably the least flattering garment ever to exist, but did that matter in the '90s? Nope.
The Overalls, Now
These days, though, your typical '90s overalls might not be such a good look. The key to making these onesies feel grown up is to find a well-fitted, more streamlined silhouette, as opposed to just breaking out your vintage pair. This chic variation embraces the trend, but without the overly baggy elements from your childhood. When paired with a classic bow blouse and a statement clutch, overalls feel intentional rather than nostalgic. Tighter, more structured ones have been popular lately among both celebrities and street-style stars, and when styled the right way, they feel anything but kiddish.

Rolla's Jasmine Overalls, $119, available at Revolve.
Pixie Market White Ruffled Sleeve Striped Shirt, $112, available at Pixie Market.
Melt Mirrored Sunglasses, $28, available at Forever 21.
L’oeil Jaclyn Slingback Mules, $72, available at L’oeil.
Photo: James Devaney/Getty Images.
The Bucket Hat, Then
Katie Holmes' look in this picture just says, "Can you even handle how cool I look right now?" With the fleecy hat and thin-framed shades, she's so ready to hang at the ski lodge. Not to mention the jean whiskers and a striped tee with just the right sliver of midriff exposed. This was a rad look at the time, we promise. But there are ways to resurface the bucket hat with much more of a cool factor. This pose is still gold, though.
The Bucket Hat, Now
Believe it or not, bucket hats aren’t just for family trips to Disney World. They’ve had a serious runway resurgence. This rag & bone version has a statement print in a neutral palette that’s easy to work into multiple outfits and styles. A button-up shirt and contrasting culottes keep the skater vibe strong. Go with a minimal sneaker and grown-up backpack to seal the deal.

Kangol Bermuda Bucket Hat, $60, available at Kangol.
Puma Sweat Culottes, $76 $39.95, available at ASOS.
Koio Collective Capri, $248, available at Koio Collective.
Oversized Denim, Then
The '90s were no stranger to over-the-top denim, from baggy jeans to full-on JNCOs. TLC, seen rocking it here at the Billboard Music Awards, went all out with Dr. Martens boots and spray-painted tees (also, that bandana!). Even though the silhouette is making a big return, from Stella McCartney to H&M, finding and styling wide-leg denim is tricky.
Oversized Denim, Now
We don't recommend wearing your jeans around your ankles, so finding a well-fitting pair is essential. Denim with a wide leg from top to bottom elongates the leg and can feel more dressed-up than a skinny or boyfriend jean. Wear it with a printed shell top and a bold but dressy pair of heels, and you're set for the office or an after-work event. The key to maintaining a grown-up feel while wearing throwback trends is to accessorize with classic, streamlined pieces that feel modern and elevate the look.

Madewell Wide Leg Crop Jean, $128 $49.99, available at Madewell.
PH5 Meadow Striped Asymmetric Tank Top, $225, available at Need Supply Co.
Gucci Dragon Leather Shoulder Bag, $3,500, available at Gucci.
& Other Stories Jacquard Mule, $125, available at & Other Stories.
Faris Linelashes, $195, available at Faris.