The worst fashion trends everyone was obsessed with the year you were born, according to experts

Blossom/NBC‘Whoa!’ indeed.
  • New fashiontrends come out with the turn of every season – they then walk off the runway into stores and finally our closets.
  • But just because something is on the runway doesn’t mean it should be in your wardrobe.
  • There have been countless fashion mishaps throughout the years, from poodle skirts to trucker hats.
  • INSIDER turned to freelance stylist and former fashion market editor at V Magazine, Scott Shapiro, to help us dissect some of the very worst fashion trends that came out of the past century.

In the 1910s, hobble skirts were all the rage, but we have no idea why. Their name tells us exactly what it was like to wear them — women were hobbling around with floor-length skirts tight around their ankles.

Hulton Archive/Stringer/Getty Images

Source: Harper’s Bazaar, Business of Fashion

Even though the shape of the skirt was thought to be flattering, the ability to step more than a few inches at a time seems like a high price to pay for fashion.

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Source: Business of Fashion, Mental Floss

Fashion in the 1920s is somewhat polarising — people either love it or hate it. Scott Shapiro, a freelance stylist and former fashion market editor at V Magazine, told INSIDER that he loves almost everything about women’s fashion from that decade, even the shoes, “which some might deem heinous.”

He said menswear, on the other hand, was laughable. “The boater hats and fedoras were tragic. Fedoras have never been and will never be OK,” he told INSIDER.

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The ’30s were quite similar to the ’20s from a fashion standpoint, Shapiro said. One trend he can’t get behind is the beachside-fashion of the time.

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“I know it was a more modest time,” he said, “but I literally will never understand why a dress with actual ruffles was seen as chic or even practical beachside attire.”

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1930s footwear was some of the worst, Harper’s Bazaar editor Lauren Alexis Fisher wrote. The T-strapped shoes seen here …

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Source: Harper’s Bazaar

… and heeled oxfords seen here were in, which is rather questionable.

Andrew Francis Wallace/Contributor/Getty Images

Source: Harper’s Bazaar

The 1940s gave us mini bowler hats. “I guess there’s a time and a place, but seeing this in photos always felt very costumey or circusy to me,” Shapiro told INSIDER.

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In the 1950s it was trendy to wear white gloves to dinner parties or fancy meals.

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Source: Harper’s Bazaar

But, as Fisher wrote in Harpaar’s Bazaar, how could anyone be expected to keep them clean?

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Source: Harper’s Bazaar

Shapiro told INSIDER that the 1950s is his least favourite decade in terms of fashion because “everything went from glam and fun to sterile, boring, and conservative.”

Hulton Archive/Stringer/Getty ImagesPictured here is Audrey Hepburn wearing a suit by Hubert de Givenchy.

“I don’t think it gets much worse than poodle skirts,” Shapiro told INSIDER. “Did people actually wear these?” Yes, they did.

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The 1960s saw a lot of loud patterns in a lot of loud colorways.

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Source: Harper’s Bazaar

Undergarments like stockings and tights were no exception here. While colour is always fun, Fisher wrote in Harper’s Bazaar that this trend was universally unflattering.

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Source: Harper’s Bazaar

A big pattern trend in the 1960s was paisley — which Shapiro told INSIDER is definitely not for him.

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“It wasn’t cool then,” he said, “especially not when done in bright colours — and I’m not sure if there’s any pattern I hate more.”

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“Why would you want to look like décor?” Shapiro asked. “I don’t even think this looks good in a décor context.”

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In the 1960s, babydoll dresses also made a splash. Fisher wrote in Harper’s Bazaar that the trend was “next-level creepy.”

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Source: Harper’s Bazaar

The 1970s was filled with maxi skirts, and Shapiro told INSIDER they’re just not a good look for anyone.

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He said that the anti-flattery of maxi skirts knows no height limit — “they somehow manage to be super unflattering and eat people alive” no matter how tall they are, he said.

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And he said some patterns — like the patchwork of the ’70s — are just overwhelming.

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The 1970s also saw the rise of jumpsuits for men, which Fisher wrote in Harper’s Bazaar was one of the worst looks from the decade.

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Source: Harper’s Bazaar

The ’80s was flooded with tacky clothing trends, Shapiro told INSIDER. In his opinion, “acid wash was the trashiest.”

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“I’m all about inventive denim,” he said, “but this moment just looks so cheap no matter what.”

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Leg warmers are paramount to any ’80s-themed outfit. But as Fisher wrote in Harper’s Bazaar, the trend makes no sense when you think about it: Do ankles really get cold during a workout?

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Source: Harper’s Bazaar

Rapper MC Hammer started sporting these iconic baggy pants in the 1980s and ’90s. Unfortunately, as Fisher wrote, even he couldn’t pull them off.

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Source: Harper’s Bazaar

Shapiro’s opinions on ’90s fashion are somewhat unconventional. “From wacky colour and pattern clashing to minimalism, sexy takes on suiting, and over-the-top Versace glamor,” he loves it all, he told INSIDER.

Jim Smeal/Contributor/Getty ImagesNaomi Campbell walks the Versace runway in 1991 wearing one of the designer’s iconic prints.

But one ’90s trend he can’t get behind is the “grunge movement” of the time.

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“Flannel is not fashion — it’s for farmers and lumberjacks,” he told INSIDER.

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The 1990s era Olsen twins may have convinced us that hats with flowers glued onto them were fabulous, but looking back now, Fisher wrote in Harper’s Bazaar that they weren’t so cool after all.

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Source: Harper’s Bazaar

Anna Wintour, editor in chief of Vogue, once said in an episode of “Go Ask Anna” that her pink leggings moment of 1993 was a mistake.

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Source: Who What Wear, Vogue

In the late ’90s, babydoll dresses had another moment. Shapiro also denounces the concept of the style. “Why would a full-grown adult want to walk around looking like a child?” he asked. Everyone from models …

Mitchell Gerber/Contributor/Getty ImagesFashion model Beverly Peele.

… to celebrities were sporting the style.

Bill Davila/Contributor/Getty ImagesLindsay Lohan

Shapiro told INSIDER that the 2000s was “arguably the worst period in fashion ever.” This decision comes mostly from his opinion of the ever-controversial Ugg boots.

Perhaps worse, Fisher wrote in Harper’s Bazaar that the idea of pairing these winter boots with jean shorts or mini skirts seems totally absurd.

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Source: Harper’s Bazaar

“Yes, they’re great and cosy and whatever … but this was literally the ‘slippers in public’ trend,” Shapiro told INSIDER. “It’s so sloppy!”

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In reality, many of us could write several versions of an ode to the velour tracksuit of the 2000s — some love letters, others with more of a loathing tone.

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Source: Harper’s Bazaar

Fisher wrote in Harper’s Bazaar that they were undoubtedly heinous — especially with the word “JUICY” written across the butt — but somehow everyone from celebs to elementary school girls was obsessed.

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Source: Harper’s Bazaar

Men tried pulling the look off, too.

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Take another look and tell us they’re not one of the most infuriating fashion trends you’ve ever seen.

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Source: Harper’s Bazaar

The 2000s “trucker” trend was equally as horrifying, Fisher wrote. Supporters donned Von Dutch hats that were half mesh with either a large patch stitched on the front or a DIY-type spray-paint job.

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Source: Harper’s Bazaar

This trend rode in right alongside the tattoo-print perpetuated by clothing brand Ed Hardy.

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Source: Harper’s Bazaar

This leads us right into all the branded T-shirts of the 2000s. Whether it had a cap sleeve or featured rhinestones, it was definitely bad, said Vogue culture editor Alessandra Codinha.

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And some people combined all those trends into one look. Vogue editor Sophie Schulte-Hillen said that she remembers sporting an Emilio Pucci scarf as a bandana, a rock and roll T-shirt, and “dirty converse” in 2002. She called this fashion mishap “resort punk.”

Dave Benett/Contributor/Getty ImagesEva Herzigova in an Emilio Pucci dress in 2002.



Headscarves proved a fickle trend in the 2000s. “I wore them in middle school in homage to the great Americana icons, but ended up looking like a Backstreet Boy,” said Vogue senior writer Mackenzie Wagoner.

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And in the 2010s we only have one question for the fashion powers that be: Why are Crocs back? Why, Balenciaga … Why?

via Balenciaga

Source: Teen Vogue

While peplum has been a design feature forever, we started seeing it everywhere in the 2010s.

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“Peplum is hands down, without a doubt, my least favourite trend to ever happen,” Shapiro told INSIDER. “It just automatically makes the wearer look like a Middle-America mall girl with horrible taste.”

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The MC Hammer pants — also more widely known as harem pants — came back via Justin Bieber in the 2010s. But as Washington Post writer and critic Jen Chaney wrote, just because the Biebs is wearing them that doesn’t make them OK.

Brian Babineau/Contributor/Getty Images

Source: Vanity Fair, The Washington Post

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