The Worst Hairstyles We Used To Love


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Mandy Moore via Instagram

Just like fashion, hairstyles come and go. Some were so timeless that we can look back at them decades later and still think we looked amazing. While others were so experimental that they almost look comical a few years after. We're going to focus on the latter and look at all of the worst hairstyles we used to love, because cringing is fun sometimes.

When you go along with trends, part of the deal is knowing you might look ridiculous once the fad is over. While crimped hair might have felt fresh in the '80s, and zigzag center parts might have looked cool in the '90s, and black streaks on platinum hair might have been mind-blowing in the new millennium, all of these hairstyles now feel dated and just a little silly. 

But if you only wore classic hairstyles, you wouldn't have nearly as much fun at the hair salon. It's exciting to experiment, even if you will look back at those styles years later and groan. Read on to see some of the worst hairstyles we used to love. From flipped layers to chunky highlights to jeweled center parts, there are a lot of doozies. How many have you worn?

Prom Curls

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Jim Smeal / Contributor

Whether it was to the middle school dance or a holiday party, the go to hairstyle for special events during the early noughties consisted of tight curls. All you needed was a one-inch curling iron and plenty of hairspray, but rather than brushing out the curls like we do today, you just left them tightly coiled. 

You could have left your hair down, or swept half of it up like Anne Hathaway did. And then for extra glamour, a quick squirt of glitter hairspray added a sparkle to your roots and crown.

Bejeweled Hair

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Dan Callister / Stringer

For those who thought glitter hairspray was too subtle, hair jewels were an easy upgrade. It had the same aesthetic as wearing a tiara in your hair, but with a new millennium spin. The jewel accents could be arranged in a variety of ways. Some, like Paris Hilton, liked to scatter the jewels across the crown, adding some sparkle to freshly straightened hair. Others liked to place them down the center (or zigzag) part, while others would stick a few choice jewels on the gelled tendrils framing their face.

Chunky Highlights

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September 14, 2004 - Doug Benc/Getty Images Entertainment

In the early 2000s, women experimented with their highlights by making them thick and chunky. Subtlety wasn't the goal, and the highlights weren't meant to look sun-kissed or natural. Instead, a few choice highlights would tiger stripe down the length of the hair, creating a high contrast. Kelly Clarkson helped to popularize the look, when she debuted dark brown hair accented with brassy blonde streaks. 

The look was edgy and fashion-forward at the time, and let women experiment with different shades and hues.

Mullet Layers

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Frederick M. Brown / Stringer

Deep, obvious layers were the look du jour in the early 2000s, and while there were a lot of different ways to wear the layers, a mullet-like look was one of the most popular variations.

The hairstyle was a mix between a mullet and a shag. The hair would sit just on or above the shoulders, and different levels of layers would be cut into the hair that was framing the face. You could either straighten those layers to give them a shattered effect, or flip them out to create a mullet-like silhouette.


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Gregg DeGuire / Collaborator

The early 2000s saw a bevvy of different women decorating their buns and ponytails with colorful chopsticks. In hindsight this was the same idea as sticking forks or spoons into your hair and calling it stylish, but 20 years prior chopsticks were seen as  a beauty accessory that could elevate a simple hairstyle.

While some added sticks to decorate a basic ponytail, others used them to hold up their hair altogether. In 2002, Hilary Duff upped the ante by wearing four chopsticks to the Nickelodeon Annual Kids Choice Awards.

Fire Engine Red Hair

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Getty Images

The early 2000s ushered in a new beauty trend that consisted of bright, fire engine red hair. Everyone from Eve to Rihanna sported the look, and it was seen as a bold color choice. The look wasn't for the shy, but rather it showed a willingness to experiment and standout. 

This hairstyle choice was the early oughts' version of the pastel or rainbow hair that we have today. Trying out unexpected color choices will always be in style, but when you look at flaming red hair today, it's hard not to think of the '00s.

Flipped Out Ends

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Jean-Paul Aussenard / Collaborator

The early 2000s loved stacked layers, and those who had bobs could really have fun with the dramatic look. Gabrielle Union's bob in 2002 is a perfect example of this. She got staircase layers down the length of her bob, with the shortest layer hitting her around mid-cheek. When straightened, the haircut looked like a shag. But when the layers were flipped outward, it created a mix between Jackie Kennedy's bouffant and Farrah Fawcett's blowout. It was one of the most popular looks of the decade, and women scrambled to copy it.

Unbrushed Curls

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Ron Galella / Collaborator

Curls never go out of style, but the way that they're made changes from decade to decade. In the '90s, women with bobs loved to create tight, springy curls to frame their face. Melissa Joan Hart's 1998 look is a perfect example of that. One-inch hair pieces were wound around a small barrel, and then arranged in all of their springy glory. Rather than brushing them out to give the curls a softer look, the objective was to hairspray them into place and give them a slight crunch.

Faux-Hair Scrunchies

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Mandy Moore via Instagram

Buns are always in style, but the late '90s and early-2000s liked to keep the ends of the hair poking out from under the hair tie, creating a spiky-haired halo around the knot. 

For those who didn't have long or thick enough hair to achieve the desired amount of spikiness, faux-hair scrunchies stepped in. Mandy Moore's look is an extreme version of that style: her blonde hair was separated into a zigzag part, and her hair was pinned back into two buns. Faux-hair scrunchies then helped give her fanned-out spikes in the back.

Feathered Bobs

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Central Press / Stringer

In 1981, a freshly engaged Princess Diana debuted a side-swept hairstyle that would became one of the reigning looks of the decade: the flicked and feathered, chin-sweeping bob. Kevin Shanley was the stylist behind what became known as the "Princess Di Cut," but the two parted ways four years later, in 1985, when they had artistic differences. 

He created the "Lady Di look" during Diana's engagement to Prince Charles. "The shape just came about gradually," he said. "It was quite a bit longer when she first came to me. I thought she'd look great with short hair, and that's what we eventually agreed upon." While it was a fun, youthful look, he never expected hysteria over it. "It was quite flattering to me, although at times I got fed up because there were so many people coming in about that one thing."

Black Highlights

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December 4, 2000 - Bauer Griffin

The early 2000s were all about experimental hair colors and high contrasts, so it was no surprise when Kelly Clarkson's brassy-blonde-and-brunette hairstyle transformed into a white-platinum-and-pitch-black variation. 

Christina Aguilera was a fan of the look in her Drrty era, when she debuted platinum blonde hair streaked with black highlights. The black highlights peeked out from underneath her blonde base color, creating a vivid contrast. This look quickly became the number one hairstyle seen inside clubs and house parties nationwide.

Va-Va-Voom Hair

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August 29, 2004 - Bauer Griffin

As we got closer to the 2010s, hair seemed to expand and grow. We began to mimic the volume of hairstyles from the '80s, but with much less hairspray and mousse. Rather than having crunchy hair and tight perms, we had massive curls and teased-to-the-ceiling crowns.

Everyone from Beyonce to Jessica Simpson sported the look, and people began to stock up on backcombs, volumizing hairsprays, and extra extensions to create thicker hair. Flattened and stick-straight hair was now seen as passe, and we all wanted the opposite: thick, luscious locks.

Gelled Pixies

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Justin Goff / Collaborator

Gel was every pixie's secret weapon during the '90s. While today pixie cuts seem to be softer and are styled in a way that doesn't advertise how much product is used, in the '90s it was all about the crunchy look. 

Women like Victoria Beckham helped to popularize the gelled pixie, which consisted of choppy layers that shot up in different directions. The hair was frozen into place, and could withstand a wind storm without being mussed.

Mall Bangs

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Barry King / Contributor via Getty

Mall bangs took Aqua Net bangs to a whole new level. The high, flipped-up, spray-hard bangs got their name "from how often they were seen at the malls," The Pantagraph explained in 1991. Teenage girls loved them, and they would make their fringe stand vertically away from their foreheads. 

The popular '80s style looked "much like a cockatoo," Phiadelphia Daily News joked in 1992. While it might have been extreme — and now induces groans when people see pictures — it was the height of chic back then.

"It was all about the height," one mall-bang-wearer recalled to Tampa Bay Times in 2003. "The higher the tease, the better. It would take a lot of curling, teasing and hair spray. I can still hear our mom hollering at us to hurry up or we would be late for school. We would drive her nuts fixing our hair." They would use so much hairspray, steam would rise from the curling iron when applied to the hair.

The trend ended around 1991, when softer hairstyles began creeping into style. "Mall bangs, that big hair style that looks like it's going to grab you, is out," The Courier-News reported that year. Girls stopped teasing their hair, and vertical bangs no longer looked chic.

The Rachel

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Getty Images / Press release

Jennifer Aniston created a whole new hair trend when she revealed her iconic layered look dubbed "The Rachel" in 1995. 

The style helped Aniston emerge as the breakout star in the show Friends, where she played the character Rachel Green. The look was created especially for the actress by stylist Chris McMillan of Los Angeles' Estilo salon. He said that he created the layered look because he was trying to grow out Aniston's bangs, and it was an easy way to blend the growing fringe. He then used rollers to help define the face-framing choppy layers. 

According to McMillan, Aniston loved the cut at first, but then grew it out because it was too hard to maintain at home. "It was an easy cut, but it needed regular trims to keep the layers looking sharp. It’s high-maintenance, not a wash-and-go style. You need to blow-dry with a round brush to help define all those flicks," he told The Telegraph. "If you aren’t someone who wants to put effort into your hair, this isn’t the cut for you."

Face Covering Bangs

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Al Pereira / Collaborator

The '90s had all sorts of different kind of fringe variations, but Aaliyah helped to popularize face covering bangs. These bangs would sit just above the chin, and would frame the face beautifully when the hair was worn up and the tendrils fell down. But if you flat ironed it just right and gave yourself  deep side part, you could also have the bangs fall across your eye and block your vision. It was mysterious, edgy, and sexy — but it was also a pain.

Shag Haircuts

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Ron Galella, Ltd. / Collaborator

Meg Ryan single-handedly brought back the shag cut in the '90s, thanks to the choppy hairstyle she wore during her 1995 film French Kiss. While "The Meg" became cemented in pop culture history, it first arose out of convenience. 

“I played a character stranded in Paris without luggage, money or a place to live, so it was a stretch to think she had much opportunity to shampoo,” she told InStyle. Her stylist, Sally Hershberger, “had to figure out hair that looked bad but sort of good all at once.”

“While we were working it out during the camera test, she punctuated some remark she was making by pulling the curling iron way over her head,” Ryan continued. “A sizable chunk of my hair had singed off and was still wrapped around the iron. I noticed the flame first. For a second Sally looked like the Statue of Liberty: frozen, torch aloft and a little green. You can’t really blame her for the iron’s overheating because of the different voltages in Europe. She was left to scissor away until we got what we got.”

The look was both causal and romantic thanks to its various flips and wisps, and became one of the defining looks of the decade.

Crunchy Up-Dos

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Jeff Kravitz / Collaborator

The '80s might have been known for their love affair with hairspray, but the '90s still very much loved crunchy hairstyles. Hairstyles might have deflated in volume, but bathroom cabinets were still stocked with hair gels, mousses, and spray bottles. And all of these products came in handy when it was time for an up-do.

Crimped Hair

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Tim Roney / Contributor via Getty

Crimped hair exploded onto the scene in the 1980s, and became a trend seemingly overnight. "Put away your curling iron. Stash your hot rollers. Today's latest look is crimped hair, those zigzagged, crinkly tresses that add fullness and mystery to the plainest of Jane locks," the Los Angeles Times wrote in 1988. "In the old days, girls would braid their hair in teeny-weeny braids overnight to achieve the crimped look. Today, modern technology has invented the crimping iron."

The look might have been around since the 1800s, and electric crimping irons might have been around since the mid-1970s, but it wasn't until A-listers like Cyndi Lauper began crimping their hair that the trend caught on.

The appeal was that it looked so different from what anyone wore the decade prior. "It's awesome and wild-looking, it looks real cool, almost Rastafarian, and it makes your hair real thick," a recent convert told Los Angeles Times. Like all other hair trends, once it was overdone, the look fell out of favor.

Half Shaved Hair

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June 28, 2009 - Frazer Harrison/Getty Images North America

Cassie put the shaved head look on the map in 2009, when she decided to shave half of her head on a whim. She posted a photo of her new look on Twitter and wrote, "Sometimes in life, you need a change … Something deeper than what you thought you were capable of … & something that will shock your mother, but make her call you a ROCK STAR." 

By 2012 a bevvy of stars had followed in her footsteps, with A-listers like Rihanna and Lady Gaga copying the look. "I think the shaved-head trend is amazing," she told MTV. "It's definitely a fun trendsetting hairstyle. Really glad that I guess I made it mainstream is maybe the right word. And it's inspiring. I like to see how other young girls remix it and add color and all of that."

High Ponytails

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Michael Ochs Archives / Stringer via Getty

High ponytails became all the rage in the '80s, thanks to pop icons like Paula Abdul and Madonna, who appreciated high, frizzy ponys. While high ponytails have been around since the '50s (the swingy, glossy versions were popular among bobby-socked teens during that era), the '80s took it up a notch. The ponytail was tied further up on the head — right at the crown — and the tail was teased, crimped, and hair sprayed. 

Nowadays, ponytails are more subdued, and usually found at the nape of the neck. Such a high pony is now only synonymous with cheerleaders and the Kardashian sisters.

Piecey Up-Dos

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Time & Life Pictures / Collaborator

In the '90s, up-dos either resembled curly poodles or messy topknots. Alicia Silverstone's 1990 look is an example of the latter, which she wore to a red carpet event. Her hair was swept up high onto her crown, and it looked like she just quickly threw it into a messy bun. The ends of her hair weren't pulled through the hair tie, and instead were artfully arranged around her head to create more volume and interest.

Teased Crowns

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Victor Malafronte / Collaborator

Posh Spice usually sported a sleek bob, but when she was feeling edgy she would give her crown some major volume. The idea was to tease the crown up to the sky, but leave the sides relatively flat so as not to look like an extra from Dynasty. It became the go-to look for nights out and when you wanted to feel sexy.

'90s Updos With Butterfly Clips

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Ron Galella, Ltd. / Contributor

The '90s were all about messy updos but Kirsten Dunst really epitomized the era with with what looked like three high ponytails with butterfly clips, and long, thick chunks framing her face.

Red & Orange Highlights

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Tim Roney / Collaborator

Geri Halliwell — aka Ginger Spice — helped to popularize the orange and blonde ginger look. She had bright orange hair that was accented with brassy blonde highlights, creating a bold and highly contrasting look. People loved the adventurous color pairing, and red-and-blonde hairstyles became popularized. Chances were you knew someone that had red and orange hair, or purple and red hair.

Shattered Bangs

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August 29, 2004 - Bauer Griffin

The 2010s introduced a new way to wear bangs: shattered. Rather than having them blunt or wispy, bangs took on a choppy look jagged ends. Ashlee Simpson was a major fan of this look, and helped to popularize the eyebrow skimming fringe. It felt new and different, but today bangs have a softer look to them.

Asymmetrical Bobs

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Ron Galella, Ltd. / Contributor

There are a hundred variations of the classic bob haircut, but in 1989 Naomi Campbell experimented with an unusual, asymmetrical cut. On one side the bob skimmed her jaw, but on the other side it barely reached her ear. It felt very avant garde and experimental, and was a go-to look for fearless and fashion-forward women.


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Art Zelin / Collaborator

Perms were all the rage in the '80s. Just about everyone had their hair coiled into tight, frizzy haircuts. While it might have seemed like everyone began to wear a perm overnight, the look became popular for a few different reasons. The first was that technology was finally ready for the look. The '80s finally had a chemical-based way to give hair a semi-permanent curl, which meant that people didn't have to spend hours playing with tongs, hair wraps, or other temporary devices. It was appealing to have a curly mop of hair for several weeks, rather than just a few hours. 

Once perms started to crop up on television screens and on red carpets, women immediately followed suit, and it became a massive hit. Perms have actually come back into style this year, but the newest version revolves around loose, beachy waves, rather than tight, springy coils.

Aqua Net Bangs

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Jim Smeal / Contributor via Getty

Wynonna Judd was the queen of Aqua Net bangs, and the '80s thought that the stiff, fluffed fringe helped give an "updated look" to tried and true hairstyles. 

In a 1992 article titled, "Teased Bangs Scream for Mercy," men lamented over how hairsprayed bangs needed to go out of style. "When you talk to them, it's like three people. You, them, and the hair," one man complained, saying that women's hair "rose above their head and then fell down wildly, as if styled with an eggbeater."

"I blow-dry it upside down, tease it out, gel it, mousse it and then spray the hell out of it," one 21-year-old told the paper of her routine. The article joked that "hairspray the size of a small fire extinguisher" was probably involved, and that the look captured suburb and mall culture. But while it was still popular in clubs and shopping malls, the article promised that the hairstyle was slowly on its way out. 
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