24 Worst Fashion Mistakes From the 1990s
For those lucky enough to experience the ’90s with rose-tinted glasses, we romanticize many things about the decade. Whether it was watching Friends, the dawn of multiple music movements, or the general anticipation that saturated the decade, we all salute the ‘90s.
While most things from the good ol’ 90s still hold up, its fashion does not. We’ve seen a rebound of styles rooted in the 80s and Y2K in the last few years, and there’s a reason why the 90s have been left out, and the decade had some bold fashion statements we don’t need to see again.
1. Leg Warmers
Sadly, leg warmers are making a comeback — but why? They had their day, and unless you desire the fresh-out-of-Zumba class look, it should stay that way.
In a 2022 article, Teen Vogue discussed how leg warmers originated in the ‘80s, but they took a step from pragmatism to fashion in the ’90s.
2. Global Hypercolor T-Shirts
Seattle was on the map in the ‘90s, especially with the arrival of grunge couture. However, the Pacific Northwest city was also ground zero for the Global Hypercolor T-shirt, a fashion item that used a Japanese-patented technology to change color with heat.
The craze fizzled after people realized they were accentuating their perspiration.
3. Parachute Pants
We can’t touch M.C. Hammer, but we can certainly blame him for parachute pants. For unknown reasons, multi-colored, elastic-fitted pajama pants became socially acceptable for daytime wear in the ‘90s. This trend has rebounded slightly in the form of hippie pants, though today’s styles are nowhere near as billowy and obnoxious as the parachute pants of old.
One can only imagine Hammer’s regret when he recalls those music videos…
4. Overalls
There are several ways to justify wearing bib overalls: if you are part of a ‘90s R&B act like TLC, work with machinery, or live in the Deep South and play a fiddle. If you are a middle-aged man who drives a Kia, likes to golf, and works in finance, questions will need answering.
Styling around overalls has changed, with multicolored corduroy fabrics having a moment in the early 2020s, but the denim digs remain the same.
5. Platform Sandals
Ladies loved wearing open-toed wedges in the ‘90s. While they looked cool, the footwear contributed to many an ankle mishap. In addition to falls and strap breakages, platform sandals were brutal to walk in.
While these shoes are still popular in the summertime today, are they worth the effort and risk? I’m not going to recover from a tumble these days with the same grace I would’ve in the 90s.
6. Bucket Hats
Bucket hats caught on toward the end of the millennium, with notable trendsetters propelling their popularity – L.L. Cool J, Jay Kay from Jamiroquai, and Run DMC. Though they’re no longer the star of the show, bucket hats never really left the stage, did they?
These hats are staples of the beach-boho VSCO girls, and modern stars like Cardi B and Rihanna have incorporated them into their wardrobes. However, if Piers Morgan wore a bucket hat in public, he wouldn’t get far without ridicule.
7. Oval Sunglasses
There is a famous press photo of young Brad and Gwyneth sporting matching oval sunglasses. In retrospect, even the stunning power couple looked silly, though I must admit I had a brief oval sunglasses phase as a teenager.
Who said a soccer shirt, cargo pants, and oval sunglasses were a bad look? The good news for comedians is that they are making a comeback.
8. DayGlo Apparel
Tetrachromacy is a rare human condition that allows its carriers to see up to 100 million colors, so the ‘90s must have been a nightmare for Tetrachromatic people. Whether it was Day-Glo socks, ski pants, or cycle shorts, it was the unofficial color palette for the ‘90s.
Although there have been flickers of a resurgence in recent times, nothing approaching early-nineties Day-Glo fashion crimes has been reported —yet.
9. Pants Under Skirts
My generation of teenage girls loved listening to L7 or The Cranberries in their bedrooms, wearing pants—usually cargo pants—under a skirt.
This look was definitely a late-nineties trend, and even though Gwen Stefani and Natalie Imbruglia made the look their own, sometimes, what happened in the ‘90s must stay in the ‘90s.
10. Full Pinstripe Suits
In the age following that of the young, urban professionals (yuppies for short), the ‘90s was a decade of big, bold statements to match the big, bold, deregulated stock market.
Wall Street may have released in 1987, but Gordon Gekko’s power suit influence lived on well into the ‘90s with the full pinstripe suit craze. A visitor to the ‘90s would have been forgiven for thinking they had taken a wrong turn, ending up in the Prohibition era.
11. Vests and T-Shirts
At the beginning of the Friends opening montage, crowdpleaser Chandler is wearing what so many trendsetters wore at the time — a vest over a white T-shirt.
The same look adorned most popular culture in the early ‘90s, and let’s be honest: it really should stay there, if anything, because the ‘90s owns it.
12. Cycle Shorts
Okay, we are firmly back in the cycle shorts territory now, and some of us are scared by this predicament. Tanned, toned skin, preferably that of an elite-level cyclist, is the only place for cycle shorts. Furthermore, women can pull the look off better than men — these are just facts.
Cycle shorts work if a man competes in the Tour de France; they don’t if he is commuting to work.
13. Giant Pants
If you owned a skateboard in the ‘90s, chances are you also owned several pairs of oversized pants, the type that covered your entire shoe. There was one significant danger involved with such a fashion choice: tripping over them.
The baggy pants look is now appearing in its new zeitgeist, the second millennium’s third decade. I honestly thought we had mastered pants, but here we are again.
14. Vintage Hats
If you were born anytime before 1990, you might remember Blossom, the five-season-long teenage biographical series about an Italian-American family. The central star, Blossom Russo, loved wearing vintage bucket hats adorned with flowers, hence the name Blossom.
This earnest, wholesome look blended into nerd-chic in later decades and isn’t returning anytime soon.
15. Plaid Suits
The plaid shirt will be eternally grateful to the ‘90s; the decade made a comfortable home for plaid lovers and never looked back. While the plaid shirt is still popular with fashionistas and indifferent hunters alike, wearing it in suit mode was a braver statement.
Nobody pulled off the plaid suit better than Alicia Silverstone in the iconic Clueless. In her honor, let’s leave plaid suits in the time they worked best.
16. Tube Socks
Thanks to their American cousins across the pond, British teenagers were obsessed with long, white Nike tube socks. However, in retrospect, they only looked good on certain people: those street-smart urbanites who can pull the look off.
Do they deserve a comeback? It’s a moot point because they are back with a vengeance in 2024.
17. Hoop Stripes
In his more innocent, pre-Slapgate career, Will Smith was everybody’s favorite fish-out-of-water sitcom star. A cursory Googling of his Fresh Prince alter ego will yield countless images of him wearing his trademark horizontal-striped T-shirt.
It may have worked for ‘90s Will Smith, but unless you enjoyed accentuating your midriff or looking like a lost sailor, let’s not bring this back.
18. Studded Accessories
Although Billy Idol was prominent in the eighties, he would have still enjoyed the ‘90s with its studded belts and purses. We’re not sure why studded belts were big in the ‘90s, and did they ever go out of fashion?
A huge heavy metal renaissance was happening in the decade, so maybe this was the catalyst.
19. Backward Baseball Caps
The backward baseball cap look must have come from somewhere, but where? Some say it was Michael Jordan in Chicago Bulls training. Baseball player Kenny Griffin Jr was so famous for his reversed cap that Major League Baseball (MLB) seriously considered giving him a backward cap plaque.
Limp Bizkit frontman Fred Durst also claimed the backward hat look in the late ‘90s; however, when the wrong person turns their cap around, palms will hit faces.
20. Fanny Packs
Fanny packs were big in Britain, and in the early ‘90s, everybody had one. I grimace at photos of this period, which show my young self wearing cycle shorts complemented by a modern-day sporran (the pouch Scotsmen wear over their kilt).
Since then, men have resorted to wearing the fanny pack over their shoulders, which is more acceptable. However, don’t wear one in its intended position unless you want to look like a tourist everywhere you walk.
21. Double Denim Ensembles
Levi’s Jeans argues that double denim can work today if done right, though I beg to differ. The denim megaliths also decree how double denim was born in the ‘70s and ‘80s, though it became hugely popular in the ‘90s, the difference being darker tones and baggier cuts.
Nevertheless, the likes of David Beckham and Gigi Hadid made it work more recently, but let’s be honest: they are David Beckham and Gigi Hadid.
22. Ugg Boots
The late ‘90s saw a renaissance in Ugg boots, first seen in 1978 in Australia and usually worn as slippers. Fast-forward to the modern ‘20s and Ugg Boots are still a mainstay for young women and men everywhere.
Few ensembles today will accommodate Ugg boots, especially outside their intended winter season, yet people persist.
23. Turtle Necks
Steve Jobs will always be credited as the man who made turtlenecks work: his body shape and tall, wiry frame suited the look. Although some may think his turtlenecks were a post-millennial addition to the former Apple CEO’s wardrobe, he famously wore a NeXT-brand turtleneck to the 1991 annual P.C. Forum gathering in Arizona.
Incidentally, that same turtleneck sold at auction for almost $3,000.
24. Velvet Tracksuits
There is a definite “expectation vs. reality” moment with velvet suits. Ladies would all love to succeed with a slinky velvet tracksuit. While the favored look for young women sitting in Business Class works for the average Kylie and Kendall, in reality, they accentuate all the wrong body parts, making most people look like adult-sized Teletubbies.
Velvet has no guilt for its aesthetic effect on innocent victims.
