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Boomers Need To Realize These Dated Fashion Trends Just Aren’t Cool

Monica November 9, 2023

Fashion trends are called trends for a reason. Most if not all of them run their course at some point. This is especially true for those fashion trends that quickly reached a peak and had their inevitable downfall. It’s hard to believe these trends existed at one point in time. Looking back, they’re all pretty cringe-worthy. It’s good that some of these fashion trends haven’t continued into modern times, even though some boomers continue to sport turtlenecks, baggy jeans, and thin eyebrows. Someone needs to tell them a thing or two about fashion, so we’re here to call out the dated fashion trends that should be left tucked in the far corners of your closet.



Back in the 1940s, turtlenecks were in. People wore them all day, every day, sporting them at weddings, birthdays, dinner parties, and just around their house. But nowadays, unless it’s the dead of winter and your neck is threatening to freeze without that extra layer, it’s best to avoid them altogether. They create an unattractive bobblehead look that makes most people look disproportionate. It’s hard to make your neck and torso look elongated when it’s covered by an outdated piece of fabric (via Reddit).


Silk Scarves

Back in the 1940s, silk scarves were all the rage. They even date back several decades when Beethoven sported those silk scarves. They are a statement piece that’s a time stamp to a much older era. But that doesn’t mean it’s continued to the present day. It can be pretty unflattering and although you might think it looks good, chances are it looks horrendous. If you carefully pair it with the right clothes, there’s a chance you’ll get an elegant look, but it’s not likely. However, the people of Reddit disagree, and some even amidst, “Scarves are excellent, and anyone who says otherwise deserves their frosty neck.” We’ll take the frosty neck, thank you very much (via Reddit).


Pearl Necklaces

For a short time in the ’50s, pearl necklaces were all the rage. Every time you see a pearl necklace, you probably can’t help but think of Audrey Hepburn in Breakfast at Tiffany’s. She sports a black dress and a pearl necklace, though nowadays, that pearl necklace just wouldn’t look as cool. If you try to wear a pearl necklace, chances are, people will think you’re dressing up as someone from the ’50s. Stone and emerald necklaces are much more popular today. As Reddit puts it, “I definitely would never wear a white pearl necklace. White pearls are currently in style for gen-z boys, copying Harry Styles’s aesthetic.” Unless you want to achieve that look, it’s best to avoid pearls altogether (via Reddit).


Kitten Heels

For a couple hundred bucks, you could buy yourself your very own pair of Kitten Heels in the 1950s. It’s neither a heel nor not a heel. They’re supposed to be training heels for kittens, or women who are not yet ready for the real deal of heels. You might as well just wear flats if you’re thinking about wearing kitten heels, or go all in and wear a regular heel. They’re outdated for a reason, and as some Reddit users put it, “I can’t stand them. Low heels are good but kitten heels are like trying to walk on sticks.” In terms of kitten heels, you should be all in or all out (via Reddit).


Square-Toed Shoes

Square toes are as frightening as ever, thanks to the Warner Bros movie The Witches. Luckily it was just a fiction movie, but that doesn’t make it any less terrifying, especially since square-toed shoes were a fashion sense in the 2000s. They’re not flattering and give off a chunky, unnatural look that’s best left as far away from our feet as possible. If you want a clunky shoe, go for one that has a rounded toe and save us all the horror. They also accentuate the shape of your foot, making them look wider and larger than normal (via Reddit).


Choker Necklaces

If you weren’t wearing a choker necklace in the 1990s, then you weren’t in on the hottest fashion trend. Nowadays, however, if you’re seen sporting a choker necklace, people might look at you funny. It’s a good thing it’s outdated because that flapper fashion doesn’t match modern times. It used to symbolize rebellion, and though Drew Barrymore once sported the choker necklace, that doesn’t mean the trend should stick around. One Reddit user’s grandpa said it makes people look like a dog without a leash. It’s best to just avoid that embarrassment and wear a different necklace (via Reddit).


Shoulder Pads

Back in the 1980s, you wouldn’t be caught without your shoulder pads. How else would you achieve that squared-shoulder look? It symbolized strength and proper posture. But instead of masking bad posture like they used to, people are turning to yoga and getting rid of the shoulder pads. If we see a boomer wearing shoulder pads, it’s best to simply remind them that it’s not cool anymore, much to their chagrin. Some people never even wore shoulder pads and cut them out before they even took the tag off their clothes (via Reddit).


Sagging Pants

Stop right there. There’s no need to show the world you’re wearing underwear, even if it’s decked out in jewels. One Reddit user said, “A guy at work wears his pants sagging. We’re in a business where dress pants, dress shirts & ties are required, I just got okayed to not wear a tie because of my new position and where my new office is.” It’s a trend that made its way through the pants of teens during the ’90s, but luckily, went out of fashion. Even one critic once said, it “looked like they were pooping themselves while they walked.” But it still’s noticeable with some old men, so you might just need to tell a boomer or two to pull up their pants and put on a belt (via Reddit).


Noticeable Pantyhose

Back in the 1980s and ’90s, noticeable pantyhose were a thing. There was once a time when it was acceptable for pantyhose to be a different shade to our regular skin, making it look like a horrible orange spray tan. Someone needs to tell the boomers that the only acceptable pantyhose is black. But we have to give them some credit, they were the spark for the billion-dollar company Spanx. Pantyhose were also the worst things to wear in hot climates, so it’s good they never made a comeback (via Reddit).



Do you remember the Croc era? These horribly colored plastic shoes were too popular for their own good. Even celebrities wore those horrendous shoes back in the 2000s. Nowadays, if you see someone wearing a pair of Crocs, you just feel bad for them. They are comfortable but that doesn’t mean they should exist. One Reddit user has an explanation, and said, “People who purchase them don’t care for style. They are buying them for practicality and comfort, like the rest of the ugly shoes out there.” Still, there are better shoes out there than Crocs (via Reddit).


Mom/Dad Jeans

Even though jeans are timeless and still very much a staple of today’s fashion, it doesn’t mean every type of jeans is cool. In fact, mom-and-dad jeans are about the worst style of jeans out there. They do nothing but give your body a boxy, squared shape. It makes your body disappear into the jeans. Even Reddit users agree, saying, “Noticed in the last couple years how all the girls are wearing high-waisted, loose-fitting light blue jeans like you would see in the early ’90s and thinking it’s a good look. We corrected this terrible fashion choice with the low-waisted skinny jeans, now we’re back to square one?” It might take some time to undo this horrible fashion trend (via Reddit).


Spray Tan

If you ever had a spray tan, you might cringe at the mere thought of once having walked around with brightly colored skin. Nowadays, we embrace a healthier look, and natural skin is definitely the best skin. There are other ways to achieve the sun-kissed look that’s better than spraying your body with chemicals just to look a little bit more orange. This isn’t Jersey Shore. Some Reddit users can’t stand the look of the spray tan, saying, “It is never a subtle transition and you are not fooling anyone. Plus, have I ever seen somebody artificially tanned that looks better afterward? The result always leaves a nasty burnt orange color. Yuck. Major turnoff. Of course, I am assuming that this is a beauty choice, please correct me if I am wrong.” In modern-day times, there’s nothing worse than that look (via Reddit).

Daily Mail

Lip Fillers

No one knows how or why people think lip fillers are a good idea, but they’re making a comeback. They’re some of the worst-looking fashion trends out as they make your lips look like balloons. The people of Reddit agree, saying “Lip fillers look like German sausages.” That’s certainly one way to put it. Let’s hope that gigantic pout is on its way out the door (via Reddit).


Thin Eyebrows

Once the thin eyebrow look made its way onto the faces of those unfortunate souls, there was no way we could ever forget them. They were a trend that started in the 1990s, and Pamela Anderson might have been the reason it all started. Nowadays, we have thick and natural eyebrows, yet there are still some boomers who still think it’s okay to wear their eyebrows thin (via Reddit).


Statement Necklaces

We’ve seen the horror of pearl necklaces, but what about those clunkier necklaces? They were popular back in the 2000s. And even though our ancestors wore statement necklaces made of clunky bones, it doesn’t mean we have to copy them. Considering how many options we have available nowadays, there’s no need to wear ugly necklaces. Next time you see a boomer wearing one, gently remind them there are better options out there. One Reddit user posted this photo on horror, admitting “That’s not a statement necklace, that’s a paragraph necklace.” Jokes aside, the trend is better left buried (via Reddit).


Plastic Flip Flops

Back in the 2000s, you could wear plastic flip-flops for under 20 bucks. Considering there are over 150 million plastic flip-flops produced every year around the world, it doesn’t mean the positives of this horrible trend outweigh the negatives. Not only do they fail to protect your feet against the elements, but they have zero support, which means your feet will probably feel sore after a couple of hours (via Reddit).


Heavy Blue Eye Shadow

There was once a time in the ’60s, ’70s, and ’80s when women decked their eyelids out with heavy blue eye shadow as a fashion statement. We feel sorry for those poor souls, influenced by the one and only Barbie. At least today’s fashion statement goes for a more natural look, though we can’t say that about everyone. There’s no time to go for the jarring Mermaid look except on Halloween (via Reddit).


Bell Bottoms

These wide-bottomed jeans were popular in the ’60s, ’70s, and ’80s, though that doesn’t mean they looked good. The hippie movement brought them into fashion, and if you were a part of that trend, you might remember the discomfort of dragging them along the ground collecting dirt (via Reddit).



The ’60s were a wonderful era of free love, peace, and rebellion. That’s when tie-dye made its way onto the scene thanks to hippies raging against war. Those of Reddit can’t help but agree, saying “Tie-Dye is ugly and I am simply baffled by the number of people and brands who are like “we’ve released a tie-dye collection”. It’s worse when they call it something stupid like “the cloud collection” or “free love collection” because then it just feels pretentious.” Somehow, tie-dye surpassed the era and sometimes rears its head in the modern world, even though it’s better left back in the ’60s (via Reddit).


Wearing Teenage Brands

Back in the 2000s, teenage brands were all the rage. If you weren’t wearing clothes from Forever 21, Topshop, or Abercrombie, then you weren’t doing fashion right. When you’re young, this fast fashion is an easy choice, especially because you don’t have to think about what to wear. But unfortunately, fast fashion does way more harm than good. Nowadays, people are more aware of the damaging effects of fast fashion, way more than they were a few decades ago. If you see a boomer wearing some cheap clothing, you might want to tap them on the back and remind them there are better choices out there. If you want to be more sustainable, head to a thrift store. But make sure to avoid some of the other horrendous choices on this list (via Reddit).


Sandals and Socks

In 2010, if you were wearing your sandals without socks, then what were you doing? Socks are meant to be worn with boots, not with sandals. Sandals are meant for warmer weather. Unless you’re in the safety and comfort of your own home in socks and sandals, just do the world a favor and take them off your feet. The users of Reddit agree, saying, “Literally it makes you look like a slob, and whenever I see a group of guys walking around in long socks and their flip flops flip-flopping in unison I cringe so hard, who decided this was a good look?” Just don’t do it (via Reddit).


Long Skirts With A Turtle Neck

Unless you’re trying to dress up as someone in the 1960s, just put the long skirts away. If they’re worn correctly, they’re very beautiful and flattering, but if you don’t wear it correctly, it can make you look like a walking rectangle. Avoid turtle necks at all costs if you’re wearing a long skirt. Even though this was popular several decades ago, it’s not now. If you want to go for the long skirt look, pair it with a crop top (via Reddit).


Jersey Dresses

Until the swinging ’60s, jersey dresses weren’t mainstream. The fabric is clingy and unflattering. If you’re going to go for the look, opt for a silk or cotton dress instead. It’s better to smooth the look and accentuate your natural shape, instead of removing your shapeliness (via Reddit).



Back in the 1940s through the ’70s, you could buy a brooch anywhere from $40 to $400. This is a classic jewel that attaches to your clothes, coat, or jacket. Even though these never really go out of style, they can make you look outdated. There’s a fine line between vintage and old. If you’re going to go for the brooch, make sure it’s simple and doesn’t scream frumpy (via Reddit).


Big Sequins

Back in the 1980s, you could buy a big sequin for a couple of bucks. They’ve been around since the 18th century when people would sew their sequins onto their clothes as a fashion statement. Back then, sequins were made of metal, but now they’re made of plastic, making them look cheap rather than fashionable and chic. You’re just less likely to see them. One Reddit user is highly opinionated about it, saying, “Ok, so like a couple of little sequins on the sleeve of a shirt or dress are fine but so many dresses are completely COVERED in sequins. That itches!! And it looks tacky!! This might just be me but dresses and shirts made of sequins should just die already.” Just leave the sequins at home (via Reddit).


Leisure Suits

No one wants to remember the polyester leisure suit. Those of Reddit explain it perfectly, saying “Let us travel back to the late ’70s, children. I give you, the polyester leisure suit and, for those less-formal affairs, the polyester jumpsuit for men. Compete for the widest flair to the pants, the thickest soled high-heeled shoes, and the lapels that’d make a pterodactyl envious.” No one wants to look like a pterodactyl, so just leave the leisure suit at home (via Reddit).


Bandage Dresses

For a few hundred bucks, you could wear your very own bandage dress. In the 1990s, this was all the rage. It’s a form-fitting dress that basically looks like bandages wrapped around your figure. Unless it’s Halloween, there’s no need to go for this horrendous look, even though some people definitely want to try to bring it back into the fashion world (via Reddit).



In the 1990s, if you were caught without your bandana, you were doing something wrong. They were worn by different people and cultures, from Hip Hop to Country. People wore them around their necks and foreheads. The people of Reddit have tried to figure out a way to bring it back, by suggesting, “If you’ve got a rugged meets refined sort of vibe you could maybe get away with cutting it into some kind of a tight wrist wrap thing. Maybe with a watch over it or something? Would definitely be a little bohemian (or whatever) but if you had that going on it could fit. (Here comes the trying-too-hard crowd.)” It’s fascinating that a small piece of fabric made such a statement back in the ’90s, even though it’s now better left forgotten (via Reddit).


Small Round Metal Glasses

It’s all thanks to John Lennon that the small round metal glasses made their way to the faces of the hippies during the 1960s. Whether you actually needed the glasses or not didn’t matter. Nowadays, most people associate those small round glasses with Harry Potter. Even though they used to be a fashion icon, they’re now better left on the shelves of convenience stores (via Reddit).


Drugstore Reading Glasses

Those drugstore reading glasses might give off a good first impression, but that doesn’t mean they look good. You can spend a couple of bucks and change up your whole look, but those drugstore glasses look as good as they cost. They can also be pretty bad for your eye health since they’re not prescription and can cause blurry vision. If you need glasses, it’s worth the price to get prescription glasses (via Reddit).



Back in the 1930s, women sported cardigans day in and day out. Some of them wore waist-length cardigans, while others wore thigh-length cardigans, the latter of which were not flattering. They give a shapeless look, and without that hourglass figure, you might look a little bit like a rectangle. It’s best to leave the cardigan at home, on your shelf, and opt for something more flattering. The people of Reddit asked if they should wear cardigans, saying “If I put on a cardigan will I catch the ugly? Do I have to find a job in a library? Please, give me advice on how to wear an article of clothing I dislike.” The boomers might want to rock the look because of how comfortable and easy cardigans are, but most of us beg to differ (via Reddit).


Floral Patterns

Unless you want to look like a grandma from the 1960s, don’t even try to wear floral patterns. These prints are tricky to pull off, and unless you do it perfectly, it’s best to not even try. Depending on the print, you can look wider or slimmer. As one Reddit user puts it, “I really like flowers and things with nature. I just really don’t like floral print clothing. They don’t really match any occasion and they look very tacky. You can’t really wear anything else with a floral print shirt, dress, or pants.” If you want simple fashion, don’t even pick up the floral print (via Reddit).


Capri Pants

Do you remember wearing capri pants? The trend started in the 1960s and even made its way to the early 2000s. Nowadays, no one is caught wearing their capri pants unless they are a boomer. They make your body look short and wide and sit awkwardly on your leg. It’s better to just wear pants that sit well on your body and either reach your ankle or your knee (via Reddit).


Ripped Jeans

For some reason, people love buying jeans that are already damaged and ripped. Even though it might give you an edgy look, what’s the point? Isn’t it better to spend that money on decent jeans that’ll actually keep your legs warm, and won’t threaten to rip more? Some unpopular opinions on Reddit agree, saying, “I hated them since I first saw someone wearing one in the early 2000s and I was shocked and appalled that they made a comeback. Not only do they look bad they also defeat the purpose of wearing pants in the first place which is to keep the lower half of your body from being soiled, especially your knees. If you’re okay with your knees or calves touching dirt just wear shorts, not half-completed pants for aesthetic purposes.” Keep the ripped jeans at home with the angsty teens (via Reddit).