17 Fashion Trends From the 1990s That Make Virginians Cringe

Every decade has its questionable moments. But the 1990s really pushed the boundaries.

It was the era of “more is more.” More neon, more denim, more layering.

For Virginians growing up back then, fashion choices were as loud and chaotic as the mixtapes we burned on our CD players.

Now, looking back at what we wore, it’s no wonder the ’80s gave us so many memorable don’ts. Let’s revisit the cringe and see just how far we’ve come.

Overalls With One Strap Hanging Loose

Overalls were everywhere in the ’90s, and somehow, the “cool” way to wear them was with one strap undone and flapping around like a fashion flag.

Whether you were a Fresh Prince fan or just wanted to stand out in the cafeteria, this trend made a big splash.

The loose strap made it look like you got dressed in a hurry, or got halfway there and gave up. Not to mention the risk of tripping over it or getting it caught on something.

It also made no practical sense. Overalls were workwear once, but by the ’90s, they were just aesthetic, and a halfway commitment to them felt… well, lazy.

Today, overalls have made a quiet comeback, but no one’s hanging straps anymore—and thank goodness for that.

Shiny Pleather Everything

Pleather—fake leather that looked plastic and felt like a hot vinyl couch—was having a moment in the 1990s.

It was used in everything from miniskirts to trench coats, and if it squeaked when you walked, you were doing it right.

TV and pop stars were often the culprits. Think of any red carpet in the late ’90s, and someone was definitely baking under a synthetic jacket that looked like it belonged in The Matrix.

While real leather has timeless appeal, pleather in the ’90s was loud, sweaty, and often smelled weird. And no, it didn’t fool anyone.

Super Thin Eyebrows and Dark Lip Liner

Technically makeup, but very much part of the ’90s fashion aesthetic. Pencil-thin brows and stark lip liner were the standard look for many women, and it was fierce at the time.

The problem? Those brows didn’t grow back. Many who tweezed them into oblivion now face the long-term consequences of this trend.

And the dark lip liner with pale lipstick? It was more “raccoon chic” than sultry.

Nowadays, fuller brows and blended lip colors reign supreme, and the extreme contrast of the ’90s look has been mostly left in the past, where it belongs.

Hyper-Baggy Jeans (Bonus Points If They Dragged)

Jeans were a big deal in the ’90s. They were baggy, saggy, and dragged along the sidewalk, collecting mud and fraying at the seams.

JNCO was the king of them all, with pant legs wide enough to hide a small dog.

Teenagers thought they looked rebellious. Parents just shook their heads.

The biggest issue? They were wildly impractical. The jeans weighed a ton, got soaked instantly in rain, and were a tripping hazard.

Platform Flip-Flops and Sandals

There was a brief moment in the late ’90s when everyone wanted to be taller… but only with foam platforms strapped to their feet.

These chunky sandals looked like someone glued bricks to your shoes. They were unstable, hard to walk in, and an orthopedic nightmare.

Yet they were everywhere. You couldn’t swing a Delia’s catalog without seeing at least three pairs.

These days, platform sandals have gotten a bit more streamlined, but those original clunky versions?

They’re best left in high school yearbooks.

Shirts Worn Over Long-Sleeve Tees

The layered look of a short-sleeve tee over a long-sleeve one was practically a uniform for American teens in the ’90s.

The more graphic designs on both shirts, the better. It was part of the grunge-meets-skater vibe that swept the decade.

But style-wise, it was bulky, sweaty, and not flattering on anyone.

Like a fashion onion, this look had too many layers, and none of them worked. Thankfully, this is one ’90s combo that hasn’t made a serious comeback.

Frosted Tips and Bleach-Blonde Bangs

Ah yes, the signature hairstyle of every boy band member, and a lot of unfortunate teenage boys across America.

Frosted tips were done with aggressive amounts of hair gel and bleach. It was part cool, part crunchy.

Somehow, this trend made it feel like every guy was auditioning for TRL, even if they were just working at the mall.

Today, we look back and wonder: What was so appealing about looking like a porcupine made of spaghetti noodles?

Tiny Sunglasses That Blocked No Sun

In a decade that loved extremes, sunglasses got… really small. So small that they barely covered your pupils.

They were more about fashion than function. And while they looked futuristic at the time, they did absolutely nothing to protect your eyes from actual sunlight.

The irony? We wore them to the beach.

Now, most Americans opt for lenses that offer both UV protection and basic coverage. Because squinting was never really in style.

Tracksuits Made of Velour

Everyone from Britney Spears to suburban moms had a velour tracksuit. It was cozy, sure—but it also looked like you skinned a stuffed animal and made it fashion.

Juicy Couture was the queen of this movement, often featuring rhinestone-covered backsides and blinged-out zippers.

The plush texture didn’t age well. These suits pilled easily, clung to everything, and turned every wash into a gamble.

While we all love comfort, modern loungewear proves you don’t have to look like a walking teddy bear to be cozy.

Wallet Chains That Meant Business

These were huge with skaters, punks, and kids who liked to pretend their Blockbuster card needed extra security.

Wallet chains jingled when you walked and could double as self-defense if needed. But mostly, they were a fashion flex that said, “I listen to Limp Bizkit.”

Functionally? They didn’t help much. They were heavy, awkward, and scratched up every chair you sat on.

Today, we’ve thankfully returned to regular wallets that don’t double as a weapon.

Bucket Hats That Swallowed Heads

Bucket hats were the go-to accessory for trying to look effortlessly cool.

Whether you were channeling a boy band or LL Cool J, these floppy hats were the icing on every ’90s outfit.

But let’s be honest: they looked like fabric helmets.

They’re making a slow comeback now, but with a sleeker update. The original versions, though? Still hard to defend.

Mood Rings and Tattoo Chokers

No outfit was complete without these accessories that screamed, “I bought this at Claire’s.”

Mood rings promised to read your emotions (but mostly turned green), and stretchy black tattoo chokers tried to be edgy… but mostly just left red marks on your neck.

Everyone had them. Everyone thought they were deep. But looking back, they were more middle school costumes than actual fashion.

They were cheap, trendy, and totally impractical. Americans have since upgraded their accessories, but a few brave souls still hang on to their mood ring for “nostalgia.”

Windbreakers in Neon Color Blocks

It wasn’t enough for windbreakers to be loud in the ’90s. They had to be blinding.

Neon greens, electric purples, and highlighter yellow were stitched together like a technicolor fever dream.

You could hear someone coming from a block away just from the swish-swish of the fabric.

These jackets were practical for rain, sure. But they also made you look like a walking traffic cone.

Most modern outerwear is a lot quieter, both in color and sound.

Crimped Hair and Butterfly Clips

If your hair wasn’t crimped, twisted, and studded with plastic butterflies, were you even a ’90s kid?

Crimping irons created zig-zag textures that no one’s hair actually needed. Add in pastel clips shaped like insects, and you had a look that said, “DIY sparkle explosion.”

It was whimsical at the time, but now it’s hard to understand how we all walked around like hair was a craft project.

Today’s hair trends aim for natural, effortless vibes—but back then, more was more, even if it meant gluing butterflies to your scalp.

Cargo Pants With Way Too Many Pockets

Cargo pants were originally designed for utility. But in the 1990s, Americans took that to absurd new levels.

Suddenly, teenagers were walking around with pants that had more compartments than a camping backpack.

Most of those pockets went unused, but that didn’t stop people from stuffing them with pagers, lip balm, and whatever random objects they could find.

They made silhouettes bulky and unflattering. But hey, at least you could carry 14 pencils and a bag of Skittles.

Turtlenecks Under Everything

Nothing said “stylish and slightly suffocated” like layering a thick turtleneck under a spaghetti-strap dress or oversized tee.

It was peak ‘90s fashion logic: take something summer-y, then stuff a wool funnel underneath it.

This look popped up in every American school photo and sitcom. And somehow, it was considered fashion-forward.