How to Make '90s Trends Work

Decades later, '90s fashion retains its white-knuckle grip. on us. The '90s were a time of major trends taking hold, from Doc Martens and crop tops to chokers being the must-have accessory. Magazines told us with breathless excitement about the new "it" items everyone would be wearing, and we immediately ran to the mall with our friends to grab some.

Nowadays, dressing with a purely '90s vibe might come off a little costume-y—we were all still learning about proportions, okay?—but plenty of '90s trends will work for your modern wardrobe. Let us show you how.

Flannel

I would perhaps skip the popped collar on your flannel shirt, but there's no denying that the '90s brought this workwear staple into the fashion spotlight. There are a million ways to wear it, but oversized with a fitted cami underneath is a classic that still nods to the decade it came from.

Overalls

Toni Braxton is working the heck out of these classic blue denim overalls, and she's wisely kept them styled simply: ribbed tee and chunky black shoes. You actually don't need to do much to update this look, beyond adding an outer layer in transitional weather and maybe opting for a slightly more pointed toe shoe.

Windbreakers

If you missed it, the '90s became the decade of the casual red carpet. Halle Berry (who was a Revlon spokesperson) is working this branded windbreaker and leggings as part of this more casual nonprofit event, but swap the crop with some flares and fashion sneakers for a perfect running errands look.

Jellies

Beloved amongst all 11-year-old girls (including Kirsten Dunst) back in the day, this style doesn't have to skew "juvenile" anymore. Modern shoemakers have updated its silhouette, so the jelly of today feels like any other sandal—just made out of plastic—and isn't so uncomfortable. It's perfect for the beach!

Baseball Caps

Goddess Pamela Anderson can make basically anything work, and the backwards baseball cap is no exception. (Do not, and I repeat DO NOT, tweeze your eyebrows that thin.) The cap is a fun "commute" accessory: Worn with a trench and sneakers, it gives off a fun, layered, casual vibe.

Pageboy Hats

Even though the pageboy hat was ubiquitous in the '00s, it had its origins in the '90s (proof, as usual, that Mary J. Blige was doing it better and before everyone else). The fuzzy hat and vest combo might feel a little dated today, so opt instead for a denim or neutral option with a coat.

Leopard

Ah yes. We loved leopard (and other animal print) as the edgy party print back in the day. (Kylie Minogue is working it, but the shoes are a no from me.) Believe it or not, leopard can act as a neutral, meaning you can pair brown or black with it—like a cardigan and boots, if you want to wear a silk dress like this.

Turtlenecks

The turtleneck was the hero piece of the '90s—we wore it with just about everything, including minis. Claire Danes gives the standard piece a little twist by scrunching it up instead of folding it over, which is a nice touch, and it would go perfectly with a blazer, sweater, or vest for some visual flair.

Minis

I'll be honest that context matters here. The mini on the '90s red carpet: Great. The mini at a party, happy hour, or event: Fine. But the outfit might feel too minimal in any context where you want to move around, sit, and eat. Opt for a sturdier strap, more substantial shoes, and an outer layer, if you prefer more coverage.

Straps

The Versace design of buckles and straps everywhere was a look if you wore it as-is. (Cindy Crawford is giving it her all, and it's doing a lot.) But a multi-strap corset top (or layering multiple tops on each other) would be a much lower-stakes way of pulling off this vibe.

Flip Flops

We provided a lot of inspiration for the "wrong shoe theory" in the '90s (i.e., wearing a surprising shoe choice that doesn't exactly match with the rest of the outfit). But for a more cohesive look, the flip-flops have to match something else in the outfit—a pair of shades, scarf, or sweater.

Crop Tops and Cardis

There was perhaps no look more popular in preppy circles than the cropped cardigan with a short, fitted camisole or tee underneath it. The modern-day iteration would have both cardi and cami be longer, with the outer layer hitting at hip level and the inner layer hitting just above your jeans.

Maxi Skirts

Maxi skirts can come in and out of fashion, but the '90s version was usually low-rise and long. Thankfully, today's maxi can be high-rise, and you should tailor it to the ankle bone or slightly lower. High enough so you're not constantly tripping over it, in other words.

Platforms

Our pop princess helped define late '90s into mid-'00s style, in part because of her schoolgirl style. Britney's relatability came from the fact that she dressed like we all were dressing, including with massive chunky shoes on our feet. Opt for black or white instead of beige, and wear them with long pants.

Messy Messy Updos

Cher! We love you! One of the many, many trends to emerge from Clueless was the character's seemingly effortless wispy updo (all the better for dramatically letting it down when needed). More hair pieces pulled back, with a host of hairpins, will look just as fun.

Surprise Hiking Boots

Specifically, as Reese Witherspoon demonstrates here, I'm referring to chunky boots paired with a somewhat "daintier" outfit. Because the shoe is more substantial, you need an equally substantial top like a blazer or coat for balance—but this shoe choice is still doable today!

Patterned Denim

I just really enjoy Cher, star that she is, literally referring to herself as such through her clothing. Fun bedazzled denim absolutely has a place in your wardrobe; Cher does it right by making it the standout piece and complementing the rest of the outfit via neutrals.

Itty Bitty Braids

There is no need to spend hours on mini braids throughout your head (unless you have the time, in which case, go forth!). A few face-framing pieces that add some visual interest to a wavy or curly style is really all you need to channel this trend without going overboard.

Pattern-Mixing

Brooke Shields serves as a forever-style icon for many of us (myself included—look at those curls!), but her particular vibe of casual-chic was particularly emulatable. The top and skirt wouldn't be two pieces you might expect to put together, but just make sure there's a similar color story and then pattern-mix to your heart's content.

Crochet

Fiona Apple was a girly-rock icon (in part thanks to her long curly hair and in part thanks to her forward-thinking style choices). Using a semi-sheer dress as an over-layer for another outfit might skew a tiny bit dated, so instead choose a chunkier, opaque knit that still has some fun details like hers.

Vests

The late singer and actor Aaliyah had top-notch fashion sense. This vest-over-coat choice is no exception, although you can swap in a collared shirt or dress underneath and achieve much the same effect. Layering classic pieces on top of each other never goes out of style.

All-Over Sparkles

Jennifer Lopez and Versace had a beautiful relationship in the '90s and beyond, and I'd argue this is the more underrated of her iconic looks. With any metallic garment, keep everything else super-simple, and keep the cut and fit classic. Just like this, in fact.

Doc Martens

There was perhaps no shoe more associated with the '90s than the black high-top Doc Marten—we wore it with everything, including (as Naomi Campbell demonstrates here) short shorts. Today they're a smart choice under jeans and trousers, but they'd pair well with a maxi too.

Preppy Vibes

The mini, the blazer, the mary janes with knee-high socks: It wasn't just a '90s trend, it was a whole aesthetic. I would probably suggest not copying this outfit in its entirety (since people will probably shout Clueless lines at you as soon as you leave the house), but keep either the socks and shoes OR the mini and blazer.

Leather Jackets

The casual, thrown-over-the-shoulder leather jacket was the fashion outerwear piece of '90s supermodels everywhere. Depending on the style, it could add a "toughness" to a lighter look (especially since grunge was all the range), and it can absolutely still do that.

Chokers

As Drew Barrymore demonstrates, a choker can be a very '70s-but-for-the-'90s vibe. (I feel less enthused by her round sunglasses, but that's a nitpick. Ditto her thin eyebrows.) Choose a necklace in a darker color, like this one, and make sure it complements something else in your outfit.

Strappy Sandals

The list of '90s Gwyneth Paltrow outfits we could wear today is long (she had very good classic style that was brilliant in its simplicity). Taking a strappy top and then telling the same story in her strappy shoes helps the outfit feel less "prom" and more "fancy dinner."

Cutesy Graphic Tees

Naomi Campbell wearing the logo of her old restaurant Fashion Cafe (at the launch party!) is extremely meta. Your graphic tee doesn't have to be on the nose—although, if you happen to have a Fashion Cafe tee lying around, I'd happily buy it from you—but make sure it's a conversation starter.

Jean Jackets

Salt-N-Pepa perfected casual style before that was a thing (just Google their matching performance costumes and you'll see how ahead of their time they were). Their signature style combined detailed, distressed denim jackets with their graphic tees for a perfect look.

A Calvin Klein Dress

The simple CK column dress (which came in mini, midi, and maxi form, and could either be a knit or satin material) was the deceptively simple standout in your wardrobe. When deployed effectively, as on Kate Moss, it helps you look elevated and also effortless all in one.

Dressing Like a 'Friends' Character

Fans of Friends obsessed over the style of the characters (particularly Monica, Rachel, and Phoebe)—to the point that you identified with one of them proudly. I was a Monica, thanks for asking. They still remain fashion icons to this day: bohemian (Phoebe), classic (Monica), and trendy (Rachel).

Airport Style

Street style has been a concept for many a decade, but celebs in the '90s used it as an opportunity to bolster their reputations as style mavens. Cindy Crawford on the way to the airport (in a less glossy, more down-to-earth outfit than we'd see in magazines) is the kind of Pinterest-worthy outfit we could emulate tomorrow.