13 Fashion Trends We Thought Were Cool (But Really Weren’t): A Cringeworthy Look Back

Fashion trends are ever-changing, and what once seemed cool often gets left behind in the past.

Sometimes you look back and wonder what you were thinking when wearing those outfits.

Whether it’s bell-bottoms from the 70s or neon leg warmers from the 80s, these trends were once the height of style but now seem questionable.

Why do some trends make a comeback while others are left to gather dust? Each decade brings its unique style that sometimes resists the sands of time.

From the funky styles of the 1960s to the bold and brash looks of the 1980s, certain fashion choices simply did not age well.

Let’s look at some of these trends that we thought were cool, but really weren’t.

1) Low-Rise Jeans

You might remember low-rise jeans from the late ’90s and early 2000s, but did you know they first appeared in the 1960s and became popular again in the ’70s? These jeans sit well below your waist, often leading to some pretty uncomfortable fashion mishaps.

Fashion icons of the time, like Cher and Farrah Fawcett, rocked them with crop tops or flowy blouses.

The style made a big comeback decades later, but it never really stopped being a nightmare for many.

You’d always find yourself pulling them up or worrying about showing too much.

In the ’70s, the low-rise jeans often came with large, flared legs.

Pairing them with platform shoes was the way to go.

By the ’80s, the rise was creeping back up, and high-waisted jeans took over, providing a more comfortable and flattering fit.

Even though they had brief shining moments in different decades, it’s safe to say low-rise jeans were more trouble than they were worth.

Fashion seems to agree, as high-waisted styles have ruled the market in recent years.

2) Ed Hardy Shirts

Ed Hardy shirts might bring back some cringy memories.

These shirts were all the rage in the early 2000s.

Sporting bright colors, flashy designs, and lots of bling, they were hard to miss.

You might remember the signature tattoo-style graphics.

Skulls, roses, and tigers were everywhere.

Christian Audiger popularized them, but the original tattoo artist, Don Ed Hardy, had a different vision.

The brand became known for being overpriced and often sported by reality TV stars.

What started as cool quickly turned into a fashion disaster.

3) Velour Tracksuits

Velour tracksuits were a big hit in the 1970s and 1980s.

They were often seen as the ultimate in comfort and style.

The soft, plush fabric made them a go-to for lounging around and casual outings.

You might remember celebrities and athletes rocking these tracksuits, making them seem super trendy.

They came in bright colors and flashy designs, making people feel fashionable and cozy at the same time.

Although they seemed great then, looking back, you might wonder why they were ever popular.

The fabric often showed sweat easily, and the look can come off as tacky today.

Despite their past popularity, they haven’t aged as gracefully as other fashion trends.

So, while velour tracksuits had their moment in the spotlight, they didn’t exactly stand the test of time.

They serve as a reminder that not all fashion trends work in the long run.

4) Frosted Tips

Remember those bleached ends that made you look edgy back in the day? Frosted tips were the ultimate hair trend.

Influenced by pop culture and famous boy bands, everyone from teens to twenty-somethings jumped on this style.

Your hairdresser would painstakingly highlight just the ends of your hair, creating a striking color contrast.

It was meant to look cool and rebellious.

Frosted tips were edgy in the ’90s, but now they’re mostly seen as a throwback to a very specific time.

Even big names like Robert Pattinson have been seen with this look, reminding us how popular it once was.

The problem? This style hasn’t aged well.

It often looks unnatural and is a high-maintenance upkeep.

Also, it doesn’t mesh well with more modern styles.

You can still find some hairstyle guides suggesting ways to make frosted tips work these days, but it’s a trend most people prefer to leave in the past.

While it had its moment, it’s one of those fashion trends we thought were cool, but realized maybe wasn’t the best look.

5) Layered Tank Tops

Layered tank tops were really popular back in the 1980s.

People would wear several tank tops, each in different colors, one over the other.

This trend was often paired with bright leggings and big hair.

You probably remember how uncomfortable it was, with all those layers making you sweat.

Not to mention, it looked bulky and awkward.

The idea was to mix and match colors, but it often ended up looking messy.

Instead of coming across as stylish, it just seemed like too much.

Looking back, it’s clear that simplicity is key.

One well-fitted tank top can look chic and put-together, without all the extra layers.

So, while it might have seemed cool at the time, layered tank tops are a trend best left in the past.

6) Crop Tops Over T-Shirts

In the 1980s, layering crop tops over T-shirts was considered the height of cool.

You’d see this look everywhere, from music videos to TV shows.

The idea was to add a bit of edge to a basic T-shirt, making it look more interesting and stylish.

The trend gained traction thanks to pop stars and athletes who weren’t afraid to experiment.

Bright neon colors were often favored, making the outfit stand out even more.

Adding a crop top over a T-shirt was meant to give off a sporty, casual vibe.

You might remember seeing people pair this layered look with high-waisted jeans or shorts.

Sometimes, the crop top would have fun slogans or designs on it.

This added an extra layer of flair to an otherwise simple outfit.

While it seemed like a fun way to express yourself, the overall look didn’t age well.

The layered effect often felt bulky and awkward.

It’s no surprise that this trend didn’t stick around for long, making it one of those fashion choices you might look back on and cringe.

7) Shutter Shades

You probably remember Shutter Shades from the late 2000s.

They were those funky, futuristic glasses with horizontal slats instead of lenses.

Kanye West made them famous in his “Stronger” music video, and suddenly everyone wanted a pair.

These shades weren’t just trendy; they became a fashion statement.

They came in vibrant colors and were seen at parties and music festivals everywhere.

Despite their cool look, they weren’t very practical.

Blocking out light was nearly impossible, making them more of a novelty item than functional eyewear.

As quickly as they rose in popularity, Shutter Shades faded away.

Today, they stand as a quirky reminder of past fashion fads.

You might still spot them at retro-themed events, but they never really made a lasting impact in the fashion world.

8) Ugg Boots with Mini Skirts

You might think that Ugg boots and mini skirts became a thing in the 2000s, but think again.

This combo first popped up in the late 1970s and early 1980s.

Trying to mix cozy boots with a short skirt led to a confusing look.

Even so, teens at the time thought it was the height of fashion.

They wore chunky, sheepskin-lined Uggs with their skirts, even though it didn’t make sense.

Mini skirts were meant for spring and summer, but Uggs were winter wear.

Looking back, pairing warm boots with almost bare legs was pretty impractical.

Despite this, some people loved the comfort and style of Uggs so much that they forced them into outfits where they didn’t really fit.

Celebrities back then even joined in on the trend, often making it seem cooler than it was.

If you look at old photos, you’ll find famous faces trying to pull off this odd mix.

9) Tattoo Chokers

Tattoo chokers were a big hit in the 90s.

These stretchy, lace-like necklaces were meant to hug your neck, giving a faux tattoo look.

They were super affordable, often costing just a few dollars.

You may remember seeing TV characters like Sabrina the Teenage Witch or Willow from Buffy wearing them.

They were everywhere in the late 90s.

While they were popular, they did have a polarizing effect.

Some loved their quirky style, while others found them cringeworthy.

Today, they pop up again in 90s-themed outfits, but the nostalgia isn’t for everyone.

Chokers have a long history, dating back to the 1600s.

Yet, the tattoo choker version is a 90s special.

They can still be found in stores today, part of the ongoing 90s fashion revival.

Despite their past popularity, they aren’t as trendy now.

But if you want to try one, it’s easy and cheap to get your hands on one.

10) Flip Phones as Fashion Statements

Back in the day, flip phones were all the rage.

You might remember the excitement of snapping one open to take a call.

They were more than just gadgets; they were style accessories too.

In the early 2000s, flip phones became a major trend.

You’d see celebrities flaunting them at events, and there were even bedazzled versions for an extra touch of bling.

But let’s be real, flip phones weren’t very practical.

They had tiny screens and limited features compared to today’s smartphones.

Yet, their retro charm has a special place in our hearts.

Even Gen Z has picked up on this nostalgia, bringing flip phones back into the limelight.

But as cool as they seemed, their actual utility was pretty lacking.

Remember the days of T9 texting? Typing out a message took forever! Despite their drawbacks, flip phones remain a memorable part of early 2000s fashion.

11) Tiny Scarves

Tiny scarves, also called skinny scarves, were a big thing in fashion during the 1960s and 1970s.

You’d see musicians and fashion icons sporting them with their outfits.

These skinny pieces of fabric were often brightly colored or had fun patterns.

In the ’60s, wearing a tiny scarf was a way to add a pop of color to your look.

You could tie it around your neck or even in your hair.

It was all about that carefree, bohemian vibe.

By the 1970s, tiny scarves were still popular, but this time they were often paired with the disco and glam rock styles.

Think glitter, sequins, and bold patterns.

It was all about standing out and making a statement.

Though they were trendy, the tiny scarves were not always practical.

They didn’t keep you warm and sometimes looked out of place with certain outfits.

Still, they had a moment in the fashion world.

12) Fanny Packs Worn as Crossbody Bags

Fanny packs were a hit back in the late 20th century.

Originally popular in the 1980s for their convenience, fanny packs were typically worn around the waist.

In the 1960s and 1970s, waist bags were simple and functional.

Then the ’80s came along, adding neon colors and bold designs that stood out.

People started wearing these packs as crossbody bags later on.

It seemed like a cool twist, right? While it may have added some fashion edge, this trend often looked awkward and out of place.

Wearing a fanny pack across your chest just never seemed practical or stylish.

It was a curious mix of a trying-too-hard fashion attempt and a desire to stand out with something retro.

Despite a recent resurgence, many still feel this trend is best left in the past.

Fanny packs are better suited for your waist, where they belong.

13) Shirt Dresses Over Leggings

You probably remember when shirt dresses over leggings were all the rage.

This trend was everywhere in the 2000s, but its roots can be traced back to the 1960s and 1970s.

Back then, shirt dresses were often seen paired with tights or leggings, creating a layered look.

It was all about comfort and a relaxed style.

By the 1980s, leggings became even more popular, and wearing them under long shirt dresses felt like a natural evolution.

It was an easy way to add modesty and warmth while still keeping a trendy vibe.

Looking back, you wonder why pairing those two items seemed like such a good idea.

The combination sometimes looked a bit mismatched and bulky.

In recent years, you might have noticed that this trend has made a slight comeback.

Lighter fabrics and better-fitting leggings have helped improve the overall look.

But if you’re ever tempted to dig out your old shirt dresses and leggings, consider how far fashion has come.

Sometimes, it’s better to leave certain clothing combinations in the past.

The Evolution of Fashion Trends

Fashion trends aren’t just random occurrences.

They are shaped by a blend of societal changes, influential people, and cultural shifts.

How Trends Are Born

Trends often start when designers introduce new styles in runway shows.

These styles get picked up by fashion magazines and influencers, making their way to the general public.

For example, the 1960s saw the rise of the mini skirt, a look that became popular thanks to designers like Mary Quant.

Social movements also play a role.

In the 1970s, the hippie movement brought bell-bottoms and tie-dye into mainstream fashion.

The 1980s introduced power suits, influenced by women entering the corporate world.

Fashion cycles through time.

What’s old becomes new again as designers find inspiration in past decades.

You might see a modern twist on 1960s psychedelic prints or 1980s shoulder pads on today’s runways.

Cultural Influences

Cultural changes impact what people wear.

During the 1960s, the civil rights movement led to more Afrocentric styles.

Dashikis and Afro hairstyles became symbols of pride.

Television and movies are also big influencers.

Shows like “Charlie’s Angels” in the 1970s made flared pants and feathered hair popular.

Music played a part too.

Think of the 1980s punk scene with its leather jackets and ripped jeans.

Global cultures leave their mark on fashion trends.

In the 1980s, Western designers began incorporating elements of Eastern fashion, like Japanese kimono sleeves and Chinese silk.

The Role of Celebrities

Celebrities have always been trendsetters.

In the 1960s, people mimicked styles worn by icons like Audrey Hepburn and Twiggy.

Hepburn’s little black dress in “Breakfast at Tiffany’s” made the LBD a staple in women’s wardrobes.

The 1970s had rock stars like David Bowie and disco queens like Donna Summer pushing fashion boundaries.

Styles became more daring and colorful.

By the 1980s, stars like Madonna and Michael Jackson were huge fashion influencers.

Madonna’s layered, lace-filled looks inspired teenage girls, while Jackson’s iconic red leather jacket from the “Thriller” video was a must-have.

Why Bad Fashion Trends Happen

Bad fashion trends are often influenced by marketing, peer pressure, and short-lived fads.

These factors can lead to styles that, in hindsight, leave us wondering, “What were we thinking?”

Marketing Hype

Companies spend a lot of money on advertisements to convince you that their products are must-haves.

In the ’60s, bell-bottoms became popular partly because magazines and TV shows featured celebrities wearing them.

The bright, bold patterns of the ’70s disco era gained traction similarly.

These items often appeared in ads showing cool, stylish people, making you want to look the same way.

Peer Pressure

The desire to fit in with your friends and peers drives many fashion choices.

In the ’80s, you might remember everyone wearing neon colors and leg warmers.

You didn’t want to be the odd one out, so you joined in.

The rise of punk fashion, with its ripped jeans and leather jackets, also saw teens and young adults adopting the look to be part of the “in crowd.”

Short-Lived Fads

Some trends catch on quickly and disappear just as fast.

Shoulder pads in the ’80s exploded in popularity, influenced by TV shows and musicians.

Nearly every outfit seemed to have massive shoulders.

Like the cowboy hats that were a flash trend thanks to certain music videos, these looks were eye-catching for a moment but didn’t stand the test of time.

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