25 Most Embarrassing Fashion Trends for Men of All Time

Posted by , Updated on May 25, 2024

Clothing has always played an essential role in human life. Research has shown that homo sapiens were probably the first humans to start using clothing around 100,000 years ago. They mostly made garments from plant materials and animal skins, primarily to keep warm during migrations to colder regions.

Fast forward a few hundred centuries and modern humans are still using clothes to keep warm. However, the reasons why people are wearing clothes has drastically changed. 

Nowadays, people wear clothes and style their hair as a way to express themselves. Over the years, some questionable fashion trends have emerged. What may have been cool and trendy back then is outright embarrassing now. Despite how horrible most of these fashion trends are, they will forever go down in history. 



Overalls, a one-piece jean garment, were created by Levi Strauss and Jacob Davis to be worn as a protective work uniform in the 1890s. Throughout the years, they were commonly worn by farmers in the southern United States.

Then in the 1960s, they became a rising fashion trend among American youth. Actor Will Smith changed up the overall fashion trend by wearing one of the overall straps behind his back.


Parachute Pants

Break Dancinghttps://www.dictionary.com/e/pop-culture/parachute-pants/

Break dancing was a cultural phenomenon during the 1980s. This new style of dancing originated in New York City. The clothing company Bugle Boy jumped in on the fad and manufactured a pair of pants that allowed break dancers more movement and flexibility.

By the mid-1980s, nondancers and dancers alike were wearing these trendy loose pants. Rapper M.C. Hammer is credited for their rise in popularity.


Frosted Tips

Frosted Tipshttps://www.maxim.com/style/frosted-tips-90s-2017-6

Historians believe that people started dying their hair back in the 1860s. Synthetic hair dye is used to cover grey hairs or as a way to simply change up a person’s appearance.

At some point in the mid-1990s, men started bleaching the tips of their hair. This new fashion trend was known as “frosted tips” or “guy lights”. Luckily, the highlighting fad began to die out around the early 2000s.


Backward Baseball Hat

Baseball Caphttp://www.dirtfork.com/wearing-backwards-hat-acceptable/

The modern baseball cap with a long peak was first worn by the Brooklyn Excelsiors in 1860. It took almost forty years for the hat to become a popular trend for everyday people. Over the years, both men and women have worn baseball caps to protect themselves from harmful ultraviolet rays.

However, that purpose becomes defeated if a person wears their baseball cap backward. The 1995 film Clueless has been credited for the backward hat-wearing trend. (And wearing it sideways is even worse.)


Skater Boy Hair

Justin Bieberhttps://menhairstylesworld.com/skater-haircut/

Teenage girls across the United States were in awe of Ryan Sheckler’s 1990s hairstyle. The professional skater grew his hair to chin length and swooped it to the side. Since then, a large number of teenage boys have been seen wearing their hair like that.

Even grown men have rocked this adolescent hairdo. Famous celebrities like Justin Beiber, Zac Efron, and Harry Styles have all had the infamous “skater boy” hair.


Puka Shell Necklace


Around the 1960s, native Hawaiians started creating jewelry out of inexpensive puka shells. By the mid-1970s, these shell necklaces were a hot commodity.  They were so popular that their price skyrocketed. Everyone wanted to have a set of puka shells to wear.

Thankfully, the peak of the puka shell craze ended sometime in the late ’90s. However, there will always be photographs that haunt the people who were captured wearing such contraptions.


Track Suits

Track Suithttps://www.complex.com/style/2015/11/history-of-the-tracksuit

Velour is a plush, knitted fabric that resembles velvet. It is created out of cotton and other synthetic materials like polyester. During the late 1970s, tracksuits made out of this material started to emerge.

The comfort of the soft texture quickly made the athletic suit a popular fashion trend. People began wearing the outfit even when they weren’t working out. Unfortunately, modern versions of the velvety tracksuit are still on the market.


Round Sunglasses

Round Glasseshttps://www.beatlesbible.com/1966/09/06/john-lennon-begins-wearing-granny-glasses/

It seems that everything centered on rock and roll during the ’60s. Round and oval-shaped glasses became a popular trend perhaps primarily because John Lennon, a member of The Beatles, was seen wearing his round glasses in 1966.

Since then, those quirky round glasses became a trademark of not only his public image but a symbol of the decade. Fast forward 60 years and people are still rocking those shades. As odd as they may look, the fashion trend has survived the test of time.


Large Belt Buckle

Large Belt Bucklehttps://www.bealscowboybuckles.com/larger-buckles-1

The majority of us have seen those chunky belts that display either a person’s name or a logo. Belts began to be used as a way to keep a person’s trousers from falling down in the 1920s.

Before then, they were mainly worn as a decorative piece. In modern society, it’s safe to say that they are now used as both a way to keep pants up and as an accessory. Overly large belt buckles are a fashion trend that should stay in the past.


Fanny Pack

Fanny Packhttps://www.theglobeandmail.com/life/style/article-once-a-staple-of-the-1990s-the-fanny-pack-is-back-in-fashion/

At the time when the fanny pack debuted in the 1980s, it was seen as a modern trend. The easily accessible fashion item was made out of synthetic material. It was created to be worn around a person’s waist.

By the 1990s, the fanny pack was appearing in popular fashion magazines like Vogue. Almost 40 years later people can still be seen wearing these small packs. It seems that the trend has returned and the style might be here to stay.


Ed Hardy and Von Dutch Clothing

Ed Hardyhttps://www.enginecommerce.com/ed-hardy-what-happened/

Christian Audigier, a French fashion designer, created both the Ed Hardy and Von Dutch clothing line. The bedazzled tattoo-inspired shirts and pants seemed to have become popular almost overnight.

During the early 2000s, a lot of celebrities wore Audigier’s brand, which led normal people to want to be part of the new trend. By 2009, the brand took in an estimated $700 million in gross revenue.

Luckily, the exotic jeweled clothing has since faded in popularity.


Popped Collar


Collared shirts seemed to defy gravity during the early 1980s. The popular fashion trend of putting the collar on your shirt straight up started an epidemic. What originally began in the United States spread to Europe and beyond.

By the mid-1990s, men all over the world were wearing their shirts with a popped collar. Celebrities and soccer stars like Eric Cantona were also spotted sporting this trend.



Faux Hawk https://www.dictionary.com/e/slang/fauxhawk/

A fauxhawk is exactly what it sounds like. The hairstyle is an imitation of the Mohawk. In the early 1950s, some jazz musicians shaved the sides of their heads, leaving just a strip of hair down the middle.

About 50 years later, people started to pick up that trend again but doing so in a way that didn’t require just a drastic change. Instead, the hairstyle was simply just shorter hair on the sides and significantly longer hair on the top. 



Square-toe Shoes

Square Toe https://www.realmenrealstyle.com/square-versus-round-toe-shoes/

Sometime in the early 1940s, the ghastly narrow-pointed-toe shoe design started to emerge. Yet the straight-line shoe didn’t become a popular fashion trend until the 1990s.

Since then, men have been wearing those types of shoes for various occasions. People have publically criticized the shoes for looking overly dorky and unnatural. A great alternative to a square-toe shoe would be a more natural, rounded toe.




Capri pants are trousers that reach down three-quarters of the leg. Their odd length tends to confuse people because they are not long enough to be pants but they are not short enough to be called shorts.

Since they have been invented, women and children seem to be the only ones who can look good wearing them. However, Europen men seem to be all over this fashion trend, so much so that men in the United States have been spotted wearing these odd-lengthed pants as well.


Tank Top


Shirts without sleeves started being worn as an everyday clothing item during the 1970s. Before then, they were commonly used as an undergarment. 

During the 1980s men could be often seen wearing their white tank top for almost any occasion. It’s believed that they became a trend because the piece of clothing was relatively inexpensive and comfortable.


Calculator Watch


The calculator watch is an accessory that proved jewelry can be both functional and trendy. It originally debuted in the 1970s and some of the most popular brands were the Casio Databank series and Timex.

Fortunately, people began to lose interest in the mathematical watch sometime during the early 1980s. Many people in today’s society have compared the embarrassing watch trend to the Apple smartwatch.

I guess we’ll just have to wait and see if that device ends up an embarrassing fashion trend.


Bell Bottoms

Jeans https://www.leaf.tv/articles/the-history-of-bell-bottoms/

During the 1960s, bell-bottoms were an essential part of a wardrobe for both women and men.

They were originally created as a functional design for people who worked on boats. However, the flared legs became a symbol of the younger hip generation.

The pants were so popular that people were spotted wearing them for the next 30 years. Today, these fabric flares at the bottom of a pair of pants can be seen as outdated.




In 2002, Scott Seamans, Lyndon Hanson, and George Boedecker came together to create a pair of shoes that would change the fashion industry forever. Crocs are a unique shoe mostly made out of foam. Despite originally being created as a boating shoe, people have used them for all sorts of occasions.

Millions of customers have raved about how comfortable and functional they are. However, they are also widely considered to be the ugliest shoes ever created.


Saggy Pants

Saggy Pantshttps://www.npr.org/sections/codeswitch/2014/09/11/347143588/sagging-pants-and-the-long-history-of-dangerous-street-fashion

Most of us are all too familiar with the saggy pants fashion trend. This odd fashion trend that leaves a man’s underwear exposed peaked in popularity during the 1990s hip-hop scene.

Years later and It’s still quite normal to see a man wearing an oversized pair of pants. Celebrities like Justin Bieber, Zac Efron, and Ross Lynch have been seen more recently wearing their pants a bit lower than normal.


Men's UGG Boots

UGG bootshttps://www.ugg.com/women/

When UGG boots start to appear, it was almost like spotting the first snowflake of winter. The American footwear company created its first boot in 1978. Since then, they’ve made an estimated two billion dollars in revenue.

The shoe is more popular among women. That could be why it’s so odd to see a man wearing a pair. Women typically wear their pants tucked into their UGGs since the shoe is quite bulky and resembles a space boot.




The Beastie Boys, an American hip-hop band, are credited for popularizing the infamous mullet hairstyle. For some reason, during the 1980s the “business in the front and party in the back” hairdo was all the rage.

Rockstars, businessmen, and even some women were getting the mullet cut. Thankfully, that fashion trend started to become the object of ridicule in the late ’90s and the hairstyle died out. Looking back at history now, it’s almost shocking just how popular it was.


Birkenstock Shoes

sandals https://www.birkenstock.com/us/sandals/

Johann Adam Birkenstock created the Birkenstock athletic sandal in 1774. They quickly became one of the most popular summer shoes amongst men and women for their flexibility and comfort. In today’s market, they can retail for a whopping one hundred dollars.

The Birkenstocks are nicknamed the “dad shoe” because, despite how comfortable they are, they look clunky and dated. A great alternative to this summer sandal would be a lightweight sneaker or boat shoe.


Chin Strap


No man should ever trim their beard in a thin line to follow their jawline. This style goes by two names: chin strip and chin strap. Not only does this beard look unnatural, but it also creates overly harsh lines that can give the impression of a double chin.

If you’re interested in facial hair but don’t want a full beard, try opting for a “five o’clock shadow.” Researchers have found that women are more attracted to men with stubble than they are to any other kind of facial hair. 


Deep V-Neck Shirts


Traditional v-neck shirts have been around since the 1960s. They were most commonly used as a men’s undershirt. Now they are being worn as an everyday piece of clothing.

A nicely ironed v-neck is a staple to any man’s wardrobe. It’s those deep v-neck shirts that men should stay away from. The shirt’s plunging neckline has been criticized for looking overly feminine.

If you are interested in showing off a little chest, try unbuttoning a few top buttons from a dress shirt. 

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