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Fashion’s creatives are constantly iterating, pushing forward on what’s considered wearable and interesting. Sometimes, the styles they debut feel controversial: unexpected, surprising, and—to many observers—unlikely to take off as a trend. (Think Crocs, bondage-inspired outfits, mullets, and UGGs.) At first glance, these styles can seem difficult to wear. But as it turns out, something about them speaks to mainstream consumers.

Below, the most controversial fashion trends that became surprisingly popular.

Hobble Skirts

The hobble skirt was a brief trend in the early 20th century. Long and slender, meant to be more daring, it was also incredibly difficult to walk in. Nevertheless, hobble skirts (so named because they’re so tight on the bottom you have to “hobble” when you wear them) have made a comeback.

Denim Bleaching

Both tie-dye (in the ’70s) and stone washing (in the ’80s) were denim trends that strategically “splotched” denim for a randomized pattern. While it might look chaotic, it’s a trend that we see over and over in new iterations. (A trend with less staying power: the Blackberry Victoria Beckham is holding.)

Microbangs

Audrey Hepburn, whose soft pixie was incredibly influential, also popularized the micro-bangs that appeared at the front of her face. We went through a period in the ’90s and ’00s where micro-bangs were horribly uneven and messy (see also: Courteney Cox in Scream 3), but a classic cut like on Mia Wasikowska is a more effective way to deploy the trend.

The Lowest Rises

Fewer trends have been more counterintuitive than the low-low-low-rise pant. Singer Ryan Starr is showing off what might be the lowest possible rise (this was in 2006, in the middle of the low-rise heyday); the modern version has more support and won’t just immediately fall off your body.

The Highest Heels

The platform heel was originally mildly popular in the ’30s to the ’50s, then achieved mainstream popularity in the ’60s through ’80s. The platform never really left us, but in the ’00s-10s it got a maximalist overhaul (Evangeline Lilly is wearing these on the red carpet in 2010).

Futuristic Fashion

Covering yourself in tight silvery material: sounds sweaty, right? Well, in the ’60s (coinciding with the Space Race and a new era of feminism), “futuristic” jumpsuits and matching separates were all the rage. Believe it or not, the “space siren” is still occasionally a thing.

Extreme Distressing

Ripped denim was initially a counter-cultural statement in the ’70s—imagine seeing cut-up clothes for the very first time, and you’ll understand how scandalous they might have been—and have come to represent everything from grunge to street fashion. Sinead O’Connor, ever the iconoclast, wore these to the 1989 Grammys!

Colorful Sunglasses

Sunglasses became more than just a functional accessory in the ’60s, which led to a vast experimentation with colors, shapes, and aesthetics. Leaving aside “shutter shades” sunglasses (remember the ones with the horizontal lines in front so that you could barely see?), a colorful pair of sunglasses is still in vogue.

Shoulder Pads

While the ’80s didn’t invent the shoulder pad, they certainly popularized it. A sharp, oversized shoulder now skews a bit dated, but shoulder pads have continued to be a major feature of blazers and coats. And a big-shouldered piece of outerwear can still create a modern shape.

The Mesh Shoe

The practical aspect of the mesh shoe is…minimal, if we’re being honest. They don’t really keep out any water or debris, and they’re exposing the whole of your foot. They became a great example of the “wrong shoe” theory, in which a surprising pair of footwear elevates an outfit (like here on Lily Collins).

Fancy Khakis

No more are khakis constrained to the realm of boring workwear! Chinos are more than a century old, but the evolution of the item’s structure, shape, and material (this is technically an asymmetric barrel denim on Victoria Federica) keep things feeling modern.

The Drop Waist

While the same cannot be said of a deep, deep v-neck (popular in the ’00s especially, like on Paris Hilton here), the drop waist has been with us since the flapper era of the 1920s. A waistline that hits at the hip can look cool and counterintuitive, and it’s a runway classic.

Patterned Tights

The “mod” subculture in 1960s London was colorful and graphic in a way that felt completely novel. Vivid patterned tights have been in the public consciousness ever since, ranging from youthful whimsy (as seen on Brooke Shields in 1983) to bright contrast to a neutral outfit.

Fluffy Shoes

Like other “non-functional” shoes, the statement is the point with fuzzy footwear. We originally spotted fur and faux-fur shoes in the ’50s, but (no surprise) Rihanna was the one to popularize the fuzzy slide in the ’10s. It’s still a fun accessory—just not in the rain or snow.

Leg Warmers

While the leg warmer might be a functional item for a dancer (it helps keep their muscles warm), it’s also entered the world of fashion as a non-functional item. Chloe Sevigny wears these as quasi-socks in 2002, and they are a popular nostalgia item.

Boxer Shorts

Wearing boxers as visible underwear (or even on their own) is somewhat of a modern conceit, even though women’s underwear has included boxer shorts for decades. It adds a touch of the “masculine” and can be worn just like any other pair of shorts, provided the material is thick enough.

The Fashion Jumpsuit

The jumpsuit was considered primarily a functional workwear piece until the ’60s, which catapulted it into women’s fashion. Ronnie Spector shows off the jumpsuit’s style from the ’60s and ’70s, but with a utilitarian construction or elongated shape it can feel a bit more updated.

UGGs

Ah yes, the fashion UGGs! The brand has been around since the ’70s, but the Y2K era gave us the incongruous “miniskirt with UGG boots” look. These days, our love of a random UGG can mean that it’s the “wrong shoe” to a more formal outfit, like we see on EmRata.

Skirts Over Pants

Perhaps one of the most controversial ’00s trend was the skirt over pants, leaving critics wondering why two separate bottoms might be joined in unholy union. Unlike the ’00s, which sometimes saw a formal skirt layered over jeans, the modern skirt-over-pants combo is meant to be complementary and cool.

Mullets

The female mullet was originally an ’80s thing (done most memorably and most successfully on Joan Jett), and then briefly reappeared in the ’00s (hello, Scarlett Johansson!). When it’s subtle, it’s actually not that intense, and the 2020s brought us some better female mullets.

Velour

The velour jumpsuit was a celebrity streetwear staple in the ’00s, another trend popularized by the likes of Paris Hilton and Kim Kardashian. Because everything comes back around, the Y2K resurgence included these soft matching separates—particularly amidst the COVID pandemic, when people were focused on being cozy.

Crocs

While only Brooke Shields can pull off Crocs to match her red carpet dress, the footwear has remained surprisingly relevant since its debut in the 2000s. They’re the platonic ideal of the “wrong shoe” theory, since it would be hard to find a more casual shoe than this.

Hanging Suspenders

Suspenders have been around for more than two centuries, and women have been wearing them for decades. But the suspenders that drape casually—serving no function but offering visual interest—is one of those trends that feels confusing but looks edgy.

The Mega-Flatform

Not to be confused with a platform heel, the flatform (a flat shoe with a thick, thick sole underneath) was popularized thanks to the over-the-top costuming on the Spice Girls. Since then, the flatform has enjoyed a slightly more subtle reinvention that allows for chunkiness without feeling like you’re about to break an ankle.

Hammer Pants

The low-crotch, baggy hammer pant was a modern iteration of the “harem pant,” an early 20th century innovation for women. It almost feels like a skirt on top (and takes on the appearance of one when stuffed into boots, as we see on Jennifer Lopez) and occasionally make an appearance in more subtle forms.

Bondage-Chic

Using the bondage/BDSM space as inspiration for clothing was daring for Versace in the 1990s (this is 1992, with Cindy Crawford in one of their more famous creations). While belts and straps aplenty might first look counterintuitive, the end product is so iconic that stars are still pulling from the archive (and otherwise being inspired by it).

Criss-Cross Jeans

It’s hard to iterate on the classic denim look (and has been attempted elsewhere on this list). But few trends were more unusual than the criss-cross jeans, with an overlapping waistband. Originally from the ’90s, the asymmetric silhouette came back in a big way as part of the popular baggy, saggy silhouette.

Split-Toe Boots

If you didn’t have any kind of fashion background, you might have looked at these boots and thought, Huh?? Putting a split between the big toe fascinated and flummoxed people at the time (Maison Margiela’s Tabi boot debuted all the way back in 1989) but they remain an object of fascination as well as a must-have for fashion experts.

The Bustier-Corset

A bustier-corset has been with us for a long time, but it was primarily seen as underwear—until John Paul Gaultier created a corset bra for Madonna’s “Vogue” video then subsequently designed all her costumes for her “Blond Ambition” tour. Thus, the “underwear as outerwear” trend took off in a major way.

Daring Pregnancy Style

Rihanna has influenced culture in myriad ways, as evidenced by the fact that she’s a billionaire beauty founder (among other things!). But before she started applying her signature edgy style to her first pregnancy, it was extremely unusual to see women debut their bare baby bumps like this. Then a whole bunch of parents-to-be started following her lead.

The Neon Root

Having visible roots has been a trend for several decades (particularly dip-dye and ombre, where darker natural roots are contrasted with lighter ends). But we’ve gotten even more intense thanks to dying the roots a totally different color—Billie Eilish’s neon roots took off in a major way, for example.

The Naked Dress

Has any garment been more divisive (and more popular) than the “naked dress”? The term was popularized in the 1960s (see also: Marilyn Monroe) and 1970s, with iconoclast Cher attending the Met Gala with some strategically placed sequins—jaws dropping everywhere, of course. Now, when we think of a daring red carpet look, a naked dress is one of the first trends that pops into our mind.