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Funky, Fun and Failed Fashion Trends Over the Years

Best Failed Fashion Trends

Funky, Fun and Failed Fashion Trends Over the Years

Fashion is a funny thing. What’s trendy today might be considered failed fashion tomorrow. If you’re still having PTSD from the traumatic trends of the early 2000s, take comfort in the fact that every other decade has also faced many questionable sartorial choices. Who doesn’t love a good stroll down memory lane… and a good laugh while you’re doing it?

Join us as we explore some of the funniest (and sometimes failed) fashion trends over the last century.

1. Saggy Pants From the 2000s

Saggy Pants From the 2000s
The saggy pants trend started in the late 90s and continued well into the new millennium (I mean, we still see guys wearing these around today). The baggy pants of the day were worn low on the hips and often revealed the underwear or boxer shorts (aka underwear) underneath. The influence of saggy pants in pop and hip-hop culture spread far beyond the music and culture that inspired it and resulted in students from many high schools being flagged for dress code violations. Luckily, this kind of embarrassing fashion trend wore itself out for the most part and has since been replaced by more form-fitting options—but let’s be real, saggy parts are still a real thing….

justin bieber

2. Shoulder Pads From the 80s

Shoulder Pads From the 80s
The 1980s was a time when the fashion industry was influencing working women to adopt many of the same sharp, defined looks as men did in the workplace. As a result, women across America were seen in “power suits” featuring large shoulder pads that made them look like linebackers. Luckily, as women began to enter the workforce in larger numbers and demand change, fashion began to reflect this new shift in roles. Eventually, the shoulder pad trend slowly faded as more women began to gain actual power in the business world—along with more freedom over their personal style.

3. Big Hair From the 80s

Big Hair From the 80s
Another oversized women’s trend of the 1980s was characterized by women wearing large, teased-up styles. Since perms, crimps, curls, and rollers often required heavy use of hairspray to keep every hair in place, big hair was as hard on the environment as it was on the wearer’s natural locks. This trend was popularized by pop and rock stars as well as television characters who wore teased-up styles. Fortunately, hair trends have since changed significantly since the 80s and early 90s, with many women now wearing natural or more simplistic styles. But, hey, if you are still rocking a high bang, you do you, boo.

4. Bucket Hats From the 90s

Bucket Hats From the 90s
The bucket hat trend was popular with both men and women in the 1990s. This trend was defined by a round, flexible hat with a wide brim, alluding to the overall bucket-like shape of the final product. Bucket hats were often made from cloth or canvas and were seen in a variety of colors and prints. This trend was popularized by sports stars, celebrities, and even models who were sure to be seen sporting a bucket hat.
At one point it might seem like the bucket hat trend had faded away, but we’ve begun to spot bucket hats on the streets recently, as nostalgic Millennials and their on-trend children look to recapture 90s vibes.
Heck, we even sell some (super cute!) 90s inspired bucket hats in our shop.

5. Poodle Skirts From the 50s

Poodle Skirts From the 50s
Poodle skirts were all the rage in the 1950s, especially among teenage girls. Most poodle skirts were made of felt and featured stitched appliques of poodles to emulate the way fashionistas of the era were often accompanied by cuddly pets. True poodle skirts featured a wide, swingy A-line shape and were usually worn with a matching blouse. The poodle skirt trend has since faded away, but it is still around today in many vintage stores as a nod to the mid century aesthetic.

6. Leg Warmers From the 80s

Leg Warmers From the 80s
The leg warmer trend of the 1980s was popular with dancers, aerobics instructors, and teenage girls alike. The era’s leg warmers were made of a variety of materials such as wool, cotton, or acrylic and came in many assorted colors and patterns. Leg warmers were often worn over a pair of leggings or shorts, but they could also be worn with nothing underneath. The leg warmer trend has since lost its popularity after being supplanted by leggings and tights.

7. Bubble Skirts From the 90s

Bubble Skirts From the 90s
The bubble skirt trend was popular in the 1990s and was characterized by a skirt that had a great deal of puffy volume in a small area. Bubble skirts were often made from a sheer or lightweight fabric and were worn with leggings or tights. Their rise in popularity may have originated from Princess Diana or Madonna, both of whom were fond of the puffy skirt. Anyone who remembers the 90s will remember these skirts—or suffer from horrible flashbacks of trying to navigate a dance class in yards of material.

8. Crocs From the 2000s

Crocs From the 2000s
Crocs were popularized in the early 2000s and are still for sale today, repopularized by their many successful collaborations with huge musicians like Justin Bieber, Bad Bunny and Post Malone as well as with fashion houses such as Balenciaga and streetwear labels like Chinatown Market.

Of course, Crocs gained most of their popularity because they are comfortable and easy to wear. However, they are fairly unattractive shoes and many still consider them one of the worst fashion trends. They might be “in” right now, but they were more often-than-not mercilessly mocked for their clunky, dare we say practical, style.

Clearly Crocs have made their comeback. These unisex classic adult clogs are one of the top sellers on Amazon Clothing, Shoes and Jewelry!

Crocs Unisex-Adult Classic Clogs
Click the image above to shop for these crocs on Amazon, you do you boo!

9. Big Sunglasses From the 2000s

Big Sunglasses From the 2000s
The big sunglasses trend was popular in the early 2000s and is still seen today. These sunglasses were often round or square in shape and could be made with a plastic or metal frame. Their unifying feature is their enormous size and the way they completely eclipse the wearer’s facial features. The big sunglasses trend was popularized by celebrities, who often wore the shades on the red carpet as well as on the streets. These sunglasses are often seen as trendy and fashionable, but one has to wonder why when there are endless shapes and styles of eyewear that would better suit the wearer’s facial features.

10. Puffy Jackets From the 90s

Puffy Jackets From the 90s
Puffy jackets were kind of a funny fashion trend in the 1990s, but for practical purposes, the trend still exists today. As you might expect, these jackets were supremely puffy and were stuffed with bulky insulation—most were filled with down and often featured a hood with fur. The puffy jacket trend was popularized by snowboarders and other winter athletes who needed a warm and weather-resistant jacket. However, after the public caught on to the trend, puffy jackets began to appear throughout the cold season on many of America’s streets. Although the puffy jacket is not flattering to most figures, some still might find them cute.

11. Backside Embroidery and Printing From the 2000s

Platform Shoes From the 70s
The “butt writing” trend was popular in the early 2000s and is sometimes still seen today on beach boardwalks, think Jersey Shore. These shorts or pants were often found in bright colors and featured writing or brand messaging on the back pocket area. While, at the time, messages like “I Love Boys” or “Too Hot to Handle” were a hilarious way to show off your personality and get a lot of laughs, that type of messaging might not get the same type of reaction today.

12. Platform Shoes From the 70s

Platform Shoes From the 70s
The platform shoe trend was popular in the 1970s. These shoes were characterized by a very thick sole that would make the wearer taller. Platform shoes were made from a variety of creative materials like wood, plastic, or even cork. Both women and men enjoyed platform shoes, but the women’s styles seemed to stick far beyond the men’s. As a result, you can still find women’s platform shoes on the market today, but they are much more discreet than what was popular in the 1970s.Some of these are wild!

13. Wide Collared Shirts From the 60s and 70s

Wide Collared Shirts From the 60s and 70s
The wide-collared shirt trend was popular in the 1970s, with fashionable men and women often enhancing the overall appearance of a standard blazer with a button-down undershirt with a wide, pointed collar. These styles were inspired by menswear, but the trend had a very androgynous look with fun and colorful designs. The wide-collared shirt trend was popularized by many musicians and celebrities of the time, including David Bowie, Jimi Hendrix, and Mick Jagger. The trend has lived on in many ways, especially with designer women’s wear. Currently, however, wide-collared shirts are more often seen as a vintage fashion worn for costumes or cosplay.

14. Denim Shorts With Exposed Pockets From the Early 2000s

Denim Shorts With Exposed Pockets From the Early 2000s
Denim shorts with exposed pockets were a huge trend back in the early 2000s. However, these days, they are pretty much seen as an outdated style trend. At the time, wearers thought it was a sexy way to elevate the basic look of a pair of denim shorts. However, we now know that exposed pockets hanging from the bottom of ultrashort denim shorts made the shorts look bulky and sometimes unflattering. That said, ask a girl in her teens or twenties and she might disagree that this is an outdated trend. I mean, Fashion Nova doesn’t want you to think so…

Fashion Nova
Fashion Nova

15. Furry Boots From the 2000s

Furry Boots From the 2000s
The furry boots trend was an unfortunate trend popular in the early 2000s. At the time, the most fashionable boots had an excessive amount of fur on the outside and were often worn as a fashion statement as opposed to protection from the elements. The furry boots trend was, in part, popularized by celebrities like Snooki from Jersey Shore, who responded to Flo Rida’s “boots with the fur” lyric in his popular song “Low.” While these boots are certainly fun and entertaining, they are not very practical—the fur does not clean or dry easily. Depending on the amount and type of faux fur, these boots can also get quite heavy. I’d say it’s safe to assume these one’s aren’t making a comeback anytime soon.

16. Lace-Up Jeans From the Early 2000s

Lace-Up Jeans From the Early 2000s
The lace-up jeans trend was popular in the early 2000s. These denim jeans had laces running up the front placket, which were used in lieu of a zipper to tighten or loosen the fit of the pants. The lace-up jeans trend was popularized by celebrities like Lindsay Lohan and Paris Hilton, who would often wear extremely low-cut versions of the garment to parties or events. Unfortunately, lace-up jeans often don’t fit well, and the laces can be a hassle to deal with. While the pants were originally intended to be a fashion statement, they are now viewed as a very outdated style. Many are glad these jeans are tied to the past.

17. Shutter Shades From the 80s (and 2000s)

Shutter Shades From the 80s
Shutter shades were a trend that originated in the 80s but came back to the 2000s. These sunglasses featured horizontal slats instead of lenses, which would give the wearer a “shuttered” look. The 2000s version of the trend was popularized by celebrities like Justin Timberlake and Kanye West, who often wore them in music videos and performances. The shutter shades trend was outdated at the time and remains even more so today. Thankfully, these impractical shades have been left behind and are no longer popular.

18. Popcorn Shirts From the 90s

Popcorn Shirts From the 90s
The popcorn shirt trend was popular in the 1990s. These shirts were made from very thin, flexible materials, which could expand and create the appearance of popcorn kernels scattered all over the shirt. When the shirt was not in use, it appeared much smaller than other clothing. However, when the shirt was worn, it would expand to the size of a normal shirt. As a result, popcorn shirts were marketed as the “one-size-fits-all” shirt. This style was popularized by celebrities like the Spice Girls, who often wore them during performances and concerts.

Outdated Fashion Trends Tend to Find a Way Back

As you can see, previous decades have provided many funny and sometimes failed fashion trends. While most of these outdated fashion ideas are seen on the streets less and less today, some vintage looks are actually reappearing and becoming popular once again.
History has a way of repeating itself, after all. If you read about fashion for long enough, you’ll notice that trends tend to repeat themselves every few years.
Still, I don’t care what ya’ll do, I will not be caught dead wearing crocs.



1.  Charles, C. (2013). Saggy Pants and Exposed Underwear: The Politics of Fashion, Identity Transactions and the Navigation of Homophobia. Identity Transactions and the Navigation of Homophobia (December 26, 2013).

2.  Ip, E., Chung, W. W. Y., Lee, S., & Schiphorst, T. (2014, June). The wearable self: Braiding a feminist critique within a somaesthetics framework for design. In International Conference of Design, User Experience, and Usability (pp. 285-296). Springer, Cham.

3.  Lockwood, T. (2010). Design thinking: Integrating innovation, customer experience, and brand value. Simon and Schuster.

4.  Prakash, J., Kotwal, A. S., Ryali, V., Srivastava, K., Bhat, P. S., & Shashikumar, R. (2010). Does androgyny have psychoprotective attributes? A cross-sectional community-based study. Industrial psychiatry journal, 19(2), 119–124.

5.  Kim, E., Fiore, A. M., Payne, A., & Kim, H. (2021). Fashion trends: Analysis and forecasting. Bloomsbury Publishing.

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