Fashion is a vibrant way we show the world who we are. It’s about personal style, keeping up with the latest looks, or finding unique thrift store gems. But what happens when a favorite style gets an unwanted makeover, not by a designer, but by a person or an event? Suddenly, a cool trend can become linked to something entirely different, sometimes even notorious. Let’s dive into 10 fashion statements that were unfortunately derailed by singular figures or moments in time.
10. Hats Off to a Trend’s Demise
It might seem surprising, but it wasn’t until 1961 that an American president chose to go hatless at his inauguration. That president was John F. Kennedy.
When JFK appeared with a bare head on that significant morning, the popularity of classic fedoras and dress hats took an almost immediate nosedive. Kennedy was, and remains, an icon of cool and charisma in presidential history. If such a stylish leader decided against a hat, many others followed suit.
The JFK Library archives even reveal letters from numerous hat manufacturers pleading with him to wear their products to revive their sales. Though he was occasionally spotted wearing a hat, it appears President Kennedy generally preferred not to cover his head. Throughout his presidency, he was rarely photographed with headwear, not even the quintessential American cowboy hat.
9. The Black Satin Curse
In 1849, London was captivated by the trial of Marie Manning and her husband, George, who were arrested for the murder of Marie’s former lover. The case became a sensation, with literary figures like Charles Dickens and Herman Melville attending their public hanging.
While the city was gripped by the story of the murderous couple, respectable women apparently wanted no association with Marie. For her execution, Marie Manning chose to wear a black satin dress. According to the Dictionary of National Biography, this choice had a dramatic effect: the material became “unpopular for many years.” The definitive historical account of the case is even titled The Woman Who Murdered Black Satin, cementing the fabric’s unfortunate link to the crime.
8. Bruno Magli Shoes: A Step Too Far
The O.J. Simpson trial was a monumental televised event, declared by a Nielson and Sony survey as the most “universally impactful” of the last 50 years. With such widespread attention, it’s no shock that it influenced some fashion perceptions—though, surprisingly, not gloves.
Following the deaths of Nicole Brown Simpson and Ron Goldman, suspicion immediately fell on Brown’s ex-husband, O.J. Simpson. The ensuing trial kept Americans glued to their screens.
A crucial piece of evidence found at the crime scene was a bloody size 12 shoe print from a Bruno Magli “Lorenzo model” shoe. At that time, only 299 pairs of these exclusive Italian designer shoes had been sold in the U.S., and O.J. wore a size 12. This previously little-known brand was thrust into a harsh spotlight. Being associated with a (probable) murderer wasn’t exactly a marketing win. It didn’t help when O.J. himself, when asked, stated he found the shoes ugly and would never have purchased them.
7. Pointed Hoods: A Symbol of Hate
Let’s be clear, pointed hoods were never exactly a runway sensation. However, when the Ku Klux Klan adopted white pointed hoods as a core part of their regalia, it became virtually impossible to see them without the immediate association of extreme racism and hatred.
The KKK, formed during the American Civil War, saw a disturbing resurgence in the 1920s. This extremist hate group is infamous for its violent acts against Black people, Jews, and Catholics, all committed while clad in white robes and these distinct pointed hoods.
The exact origin of the KKK’s pointed hood is debated. Some theories suggest it was inspired by the Spanish capirote, while others point to old Southern Mardi Gras attire. The designer of the KKK’s uniform remains unknown, but their creation single-handedly tainted any similar style. As the Anti-Defamation League notes, “the hood and robes of Ku Klux Klan members are the most visible Klan symbol of all,” making the image of the hood itself a potent symbol of hate.
6. The “Can-I-Speak-to-the-Manager” Bob
The name “Karen” has taken a sharp dive in popularity, thanks to the Gen Z slang term. A “Karen” is now widely understood as an entitled, often middle-class white woman. From jokes about demanding to “speak to the manager” to accusations of racist behavior, “Okay, Karen” has become a sharp insult.
Beyond those actually named Karen, another group has been hit by this stereotype: women with bob haircuts. Specifically, the choppy bob, often with blonde highlights, has been dubbed the “can-I-speak-to-the-manager haircut” or simply the “Karen haircut.”
This association largely began with Kate Gosselin, star of the reality TV show Jon & Kate + 8. She sported an iconic bob featuring a dramatic asymmetry between the front and back. As her public persona became known for being demanding and entitled, her hairstyle inadvertently became the visual shorthand for the “Karen” stereotype.
5. Tesla: Driving a Statement, Intended or Not
A car is more than just transportation; it’s often a statement, a way to express oneself, and sometimes, a display of wealth. In that sense, it’s a form of fashion, so it earns a spot on this list.
Few car brands have made as big a splash in recent years as Tesla, the electric car company that has been rapidly gaining traction since 2008. While Teslas are undoubtedly better for the environment than typical gas-powered vehicles, some potential buyers hesitate due to their feelings about the company’s CEO, Elon Musk.
Musk is a polarizing figure for various reasons, including his acquisition and rebranding of Twitter (now X) and his perceived support for controversial speech on social media. Consequently, driving a Tesla can sometimes lead to assumptions that the owner endorses Musk and his actions, turning the car itself into an unintentional political or personal statement.
4. Skinheads: A Subculture Stolen
The term “skinhead” carries a complex and often misunderstood history. It originated as a 1960s working-class youth movement in London that rejected mainstream conservative values. Their look was defined by closely shaved heads and utilitarian or grunge-style clothing, emphasizing a punk aesthetic. This version of skinhead culture peaked in the 1980s, a time of high political tension in Britain. This tension led to a split within the culture: some skinheads aligned with far-right groups like the National Front, while others moved in staunchly anti-racist directions.
By the 1990s, the skinhead fashion—the shaved heads, boots, and Harrington jackets—became unfortunately popular among neo-Nazi groups in America. Despite efforts from groups like Skinheads Against Racial Prejudice (SHARP) to reclaim the image and emphasize that not all skinheads were racist, the term and its associated fashion have been heavily tainted by the connection to white supremacy and racism.
3. Red Hats: More Than Just Headwear
Perhaps one of the most divisive U.S. presidents in recent history, Donald Trump’s supporters are often identified by their bright red baseball caps emblazoned with “Make America Great Again.” For many, wearing these MAGA hats is a proud display of support for the 45th president.
However, for others, these hats evoke feelings ranging from annoyance to deep offense. A New York Times article titled “Does This Red Cap Make Me Look MAGA?” shared the story of a Cincinnati Reds baseball fan who felt uncomfortable wearing his team’s red hat. He didn’t want to be mistaken for “something that I’m not, or that I represent something that I think has become pretty ugly.” The article also noted a decline in the purchase and wearing of plain red caps by many Americans, fearing they’d be misidentified as Trump supporters.
Even one Trump supporter admitted he stopped wearing his MAGA hat due to negative reactions, stating, “it always gets a look and a sneer.” While the political climate may shift, for now, a simple red hat often carries significant political weight that’s hard to overlook.
2. Trench Coats: A Dark Association
American schools were forever changed in 1999 after two seniors in Columbine, Colorado, tragically killed twelve students and one teacher. The name “Columbine” became synonymous with school shootings, and so did an unlikely item of clothing: the trench coat.
Both perpetrators, Eric Harris and Dylan Klebold, wore black trench coats on that devastating day. The long, bulky nature of the coats allowed them to conceal weapons. They were also known for frequently wearing trench coats at school and were reportedly part of a clique known as the “Trench Coat Mafia.” This group used their distinct clothing style to set themselves apart from the “jocks” and popular students who they felt bullied them.
In the aftermath of Columbine, trench coats became viewed with suspicion. Many American schools went as far as to ban them. In 1999, CNN reported on parents across the country lobbying to ban trench coats and all-black clothing in schools, deeming them “gang related.” There was also concern that the shooters’ unique style might have contributed to their being bullied, which was then linked to their violent actions.
1. The Toothbrush Mustache: Erased by Evil
More infamously known as the Hitler mustache, this short, blocky style of facial hair went out of fashion for a very clear and chilling reason.
Before Adolf Hitler co-opted it, the toothbrush mustache was actually popularized in the United States by comedians like Charlie Chaplin and Oliver Hardy. Many men appreciated its ease of maintenance compared to older, fuller styles like handlebar or walrus mustaches. It was seen as a modern, sleeker look.
The style gained popularity in Germany in the early 1900s, partly due to American visitors, and began to replace the longer Kaiser mustache (sported by Wilhelm II). It’s likely Hitler simply adopted the toothbrush mustache because it was fashionable during his youth.
However, another theory exists. Author Alexander Moritz Frey, who served in the same regiment as Hitler during World War I, claimed Hitler trimmed his mustache down to fit his gas mask properly—a plausible idea, given Hitler was hospitalized due to a poison gas attack during the war. By the 1940s, the toothbrush mustache was no longer associated with American modernity or silent film stars. It became the indelible mark of arguably history’s most evil figure. Though some have attempted to reclaim it, Hitler’s shadow looms large, ensuring you’re unlikely to encounter many men sporting this style today.
As we’ve seen, fashion isn’t just about aesthetics; it’s deeply intertwined with culture, history, and perception. These ten examples show how quickly a popular trend can be redefined, sometimes by a single individual or a pivotal moment, leaving an indelible mark on its legacy. Style is ever-evolving, and so are the stories it tells.
Which of these ruined trends surprised you the most? Do you know of any others? Share your thoughts in the comments below!
