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Fashion history is full of fabulous fads…and absolute flops. If it were up to me, these fashion trends would stay six feet under. But for one day only, we’re unearthing these past faux pas and ranking each decade by its most ridiculous fashion trend, starting with the worst of them all.

I might have started the millennium as a kindergartner, but thanks to my older sisters’ influences, even my innocent eyes remember the many whale tails that crossed red carpets throughout the 2000s. While I’m not here to police anyone’s bodies, I think we can all agree that hiking a dental floss-thin thong all the way up and over your hips is a one-way ticket to wedgieville.

The 2000s were chock full of cringeworthy fashion trends, but whale tails are the most ridiculous of the bunch.

The 1980s were just as full of regrettable fashion fads as the 2000s, but the one that I think takes the cake is Lycra workout wear. We’re talking micro unitards hiked over sweat-inducing tights in hypnotic, clashing patterns.

If there’s one thing in this world I hate, it’s sweating a lot, and just looking at these suffocating stretch outfits makes me perspire. I prefer my fashion fads to come with zero heat-stroke risk, thank you very much.

Related: All the Style Choices I Regret Making in the 80s & 90s

We may only be halfway through the 2020s, but I’m confident that nothing in the next five years will surpass the regret-in-the-making that are barrel jeans. You cannot convince me that trying on a pair of these pants doesn’t immediately turn you into a rodeo clown.

While I’m all for experimenting with silhouettes, barrel jeans take an unquestionable classic and make it worse for no reason.

If 1980s snow bunnies are a testament to anything, it’s that skiing and fashion go hand-in-hand. Long before fluff-covered collars warmed up vacationers at mountain lodges, adventurers in conical “pixie” hats were shredding the slopes.

Utilitarian fashion in the 1940s, necessitated by wartime rationing, didn't exactly lend itself to wacky trends, but knitted pixie hats are a surprising contender. Though wearing one won’t quite turn you into a conehead, it definitely takes your noggin out of the stratosphere.

Another high contender in our ridiculous fashion rankings is the bullet bra, most popularly seen in the 1950s. While Madonna put a sultry spin on the conical shape a few decades later, milder points were worn by women of all ages.

Naturally, a piece of clothing that’s as much of a potential danger to unsuspecting eyes as the air rifle in A Christmas Story was destined to settle towards the top of our list.

From fringe and suede to jean vests and bell bottoms, there are more 1970s fashion moments that I love than ones that I don’t. That being said, one fashion flop — and oh boy, do I consider it a flop — is terrycloth clothing.

Rompers, shorts, sweaters, you name it, they made it out of terrycloth. Not only does the fluffy fabric look unnecessarily bulky and pill horribly in the wash, but it’s also one of the most inexplicable fashion choices from the era.

While you might as well be wearing a towel, at least towels are more comfy than the top contenders on our list — a fact which puts this fashion flop in the middle of the pack.

Related: Our Favorite Vintage Trends Making a Comeback in 2025

As a ‘90s kid, I’m well aware of the interesting fashion choices from the final decade of the 20^th century. Yet, the one that still puzzles my brain is stirrup pants. These ultra-secure pants, often worn with oversized shirts, harken back to equestrian uniforms. But if the straps served a real purpose, they’d be less bizarre.

I mean, what suburban mom racing through the grocery store needed her pants to lock in on sport mode just to snag those weekly deals?

As someone who started high school in 2010, I’m intimately aware of the many fashion mistakes we made coming out of the naughties. But the crime I, and most of my high school friends, committed was wearing high-low hemlines, especially for formal dances.

These geometric nightmares were the definition of “why not have both?” and they weren’t better for it. I distinctly remember picking out my Homecoming Court bodycon dress paired with a wispy net high-low overskirt and feeling like the height of fashion.

However, the pictures don’t lie. It doesn’t matter how fond I was of them at the time — they’re a fad that should stay buried.

If what you know about Edwardian fashion starts and ends with Titanic, you might not know what a hobble skirt is. Paul Poiret, an iconic French designer, was the creative mind behind hobble skirts — a style of dress and skirt that cinched around the ankle to an almost immovable degree.

Did they replace more functional styles? No. Are they one of the weirdest fads from the decade? Absolutely.

Considering that you can find direct hobble skirt inspiration in vintage and modern mermaid silhouettes, this one isn’t as ridiculous as some of the others in our grab bag. Hence its lower place on our list.

At the outset, the idea of a paper dress conjures up images of thin paper gowns at the dermatology office. Yet, psychedelic patterned paper dresses were a unique, cost-cutting alternative in the 1960s.

Granted, these were always meant to be trashed after a few wears, so hygiene wasn’t exactly a major concern. Despite paper dresses being undeniably silly-sounding, there’s something inherently anti-consumption and sustainable about them that makes them almost cool in a capital C way.  

Related: 8 Ways to Step Up Your Style in 2025

Deadly economic turmoil notwithstanding, the 1930s were an incredibly fashionable decade. There aren’t many faux pas to bring to our list, but one controversial sleeve pattern has enough detractors to make the cut.

Dolman sleeves (aka batwing sleeves) are draped sleeves that extend from the shoulder seam to about the waist in a giant triangle. Hence the name “batwing.” They’re an acquired taste, but can be stylish in the right context, so they don’t deserve to rank too high on our list.

The most charming, ridiculous fashion trend on our list comes from the 1920s. With rising hemlines and daring cultural trends, many women wanted to sauce up their outfits. Their medium of choice? Paint.

Painting pictures on your stockings for a sultry peek-a-boo if you flashed your gams while dancing is a DIY trend I can get behind.

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What do these fashion eyesores all have in common? They were well past their expiration date from the moment they popped up. 

While you’re contemplating what fashion horrors the future may bring, discover which style makes your horoscope sing.