Why Rich People Dress Broke And Broke People Dress Rich

What’s with these class-based fashion trends?

Fashion today is veering in one of two directions: On one end of the spectrum is hobo-core: the uber-wealthy are splashing out on outfits artfully distressed to look like they’re old and worn. On the other end is old money, as people take to Shein to buy items that look like ultra-fancy couture but in reality aren’t designed to be worn for more than one season, or in some cases more than once. So why are the rich dressing like they’re poor and those with lower incomes dressing like they’re rich? The urge to use clothing to pretend you’re from a different socioeconomic background goes back centuries, and often the two trends do cross over: There’s long been a pattern of the truly wealthy underplaying their wealth in their fashion, while strivers or the nouveau riche show off their money in ways the established rich deem gauche. Yet today’s hobo-core look is going to an extreme that’s a little shocking in its insensitivity, and the old money look has its own set of issues worth exploring. Here’s why these class-crossing fashion trends are so in right now, what their histories are, and their biggest problems.

How POVERTYCORE became a thing

One of the earliest and most famous examples of ‘poor chic’, as sociologist Karen Halnon calls it, is French Queen Marie Antoinette’s ‘peasant play’ on her idyllic recreation of a farm. While she peacefully roleplayed, outside of the palace she was hated by the French people because of her obscene spending and was eventually beheaded during the French Revolution. That’s not the last time royalty seriously misread what’s appropriate. Prince William was photographed dressed as a ‘chav’ when he was at Sandhurst which the UK’s Guardian newspaper called out as part of a cultural shift towards demonizing poor people.

Even more influential in our modern society, the fashion industry has also long chosen to find inspiration in uncomfortable places. In the early ‘90s, Marc Jacobs ushered in a new era with his Grunge collection for Perry Ellis. Heroin chic followed – a glamorization of the gaunt, emaciated look of a drug user that became so intense President Bill Clinton spoke about it.

It was followed in 2000 by John Galliano’s ‘Homeless’ collection for Dior Couture. Models stomped down the catwalk wrapped in newspaper, accessorized with trash like battered cutlery and miniature bottles of whisky. The collection was lauded by some fashion writers, but it horrified others. Cathy Horyn, a fashion writer at The New York Times, wrote “‘Of course, it’s hard to imagine a couture client shelling out $25,000 for a dress just so she can look like a bum.” Yet it did trickle down – notably into the fashion of Mary-Kate and Ashley Olsen.

The 2000s saw the rise of the casual tech CEO in the hoodie; as Tom Searcy wrote in 2011, “it’s a status symbol to dress like you’re homeless to attend board meetings.” Meanwhile, ‘hobo chic’ has gone even further, since – later on in the 2000s, Chen Guorong emerged. He was a person without housing in China who was known as ‘Brother Sharp’. He was photographed and went viral for what many perceived to be his great sense of style. Young Chinese men copied his look – and it made it onto European catwalks too, most notably Dolce and Gabbana. More recently, along with Balenciaga and Maison Margiela releasing heavily distressed sneakers, Kanye West (whose fashions, despite his wealth, have always been about casual attire like sneakers and sweats) posted an Instagram saying we should ‘look to the homeless’ for design inspiration. It understandably seemed like a moment of parody – of life imitating art, imitating life – because the movie Zoolander had already parodied Galliano’s ‘Homeless’ collection with evil designer Mugatu’s collection Derelicte.

While trends are cyclical, and Y2K is back, it still feels a little shocking that we’re willing to revive harmful trends like Galliano’s homeless chic, given how much more socially and culturally aware young generations are now.

Dressing like you come from OLD MONEY

Beginning in Ancient Rome, there were actual laws in place to stop people from attempting to dress above their station, which prevented anyone who wasn’t part of the gentry from wearing silk or velvet, or having gold or silver embroidery on their clothing. But later, these patterns started to shift, allowing for more fluidity.

For decades, young girls have been taught by Disney and culture at large to aspire to become an imagined ‘princess’ figure. Disney princesses often adopt a reimagining of medieval clothing – from the same era as Roman sumptuary laws. But even though the princess figures are always deemed special, Disney essentially makes them feel accessible, too – because anyone can become a princess if they’re just pretty and kind enough. And there’s an element of believing this, even in adults - with many wondering why the world of Bridgerton is behind us.

It’s not just little kids dressing up as princesses – the Old Money aesthetic that’s currently viral on TikTok draws from other elements of culture, too. For example, Clueless recently leapt back into the style psyche, with multiple copies of Cher’s yellow suit flooding the high street. It showed that many have a desire to dress in the nostalgia of a 90s idea of the ultra-wealthy. And there’s also the fact that many heirs and heiresses lead glamorous, well documented lifestyles – from Nicola Peltz to Prince Harry.

Sophia Richie, daughter of Lionel Richie and sister of former It Girl Nicole Richie, recently sent ‘old money’ social media ablaze with her wedding looks. Demure and classic, lovers of the aesthetic scrambled to claim that this is the look classy women should strive for, not gaudy logomania… and then, days later, Sophia stepped out in head-to-toe Chanel logos, causing those same commenters to have to do a bit of updating to their old money definition.

The whole conversation about Sophia’s wedding week outfits really hits home the fact that what draws people to the “old money” aesthetic isn’t really the clothes themselves, but the idea of being able to style yourself visually as someone who is societally powerful. This is especially made clear by the fact that many people that are touted as being icons of the old money aesthetic today aren’t old money at all!

But the fact is, money isn’t an aesthetic – it’s not something that can be achieved by creating the right fit. So what’s the appeal?

Why Everyones playing dress up

In fashion, there’s a tendency towards what fascinates or shocks us - and often that’s also what scares us. We ‘amplify threats in society’ with our clothing (FOLK DEVILS, NEWS ICONS AND THE CONSTRUCTION OF MORAL PANICS: Heroin chic and the amplification of drug threats in contemporary society: Journalism Studies: Vol 9, No 6 (tandfonline.com)) according to Bryan E Denham, a Professor of Communications. And that’s been around since the Cold War – when even swimsuits derived their names from nuclear test sites: that’s why it’s called a ‘bikini, FYI’. So it makes sense that, in times of extreme disparity between rich and poor, we look to both ends of the spectrum for inspiration. However, in the examples of both historic and present-day hobocore and old money aesthetics, there’s a tendency to massively romanticize the original inspiration. There’s a disconnect between what it is or was actually like, versus what designers and customers end up with.

John Galliano’s ‘Homeless’ collection for Dior is a sharp illustration of that. The idea that the homeless population of Paris had chosen to live on the street apparently absolved Galliano – and his customers – of the need to interrogate inequality, or enter into a conversation with these people. The pillaging of inspiration never goes two ways – the people who are taken from often aren’t allowed access to the culture they inspire; there isn’t a trickle-up. It’s the same with the current trend of distressed sneakers, which takes its inspiration from grunge culture; the people who inspire the trends aren’t given a pass to the elite fashion circles that wear them.

That inequality is perpetuated by the fashion industry itself. The way that distressed looking clothes are made is very harmful to garment workers. When distressing jeans, for example, tiny fibers are released and can be inhaled by workers, who subsequently suffer from serious lung damage as a result. The other issue is that, when we buy new outfits that are made to look old and worn, we miss the opportunity to partake in fashion sustainably. Thrifting clothing and re-wearing, repairing, or repurposing items from our existing wardrobes is a much more ethical way of dressing. And ironically, it’s often what the oldest money people do – buy something once and make it last.

Meanwhile, the old money aesthetic exacerbates other problems. The fake handbags people buy when they’re trying to emulate the look often fund terrorism. And the horrific conditions that garment workers are subjected to in service of fast fashion are widely documented. A decade after the Rana Plaza collapse, the deadliest catastrophe in the history of clothing factories, little has changed in terms of safety, or exploitation. So when it comes to our attempts to emulate the super-rich, we actually open up more conversations about our wealth in general, in the West.


The fashion industry is built on inequality and exploitation. Fashion writer Bronwyn Seier wrote in 2020 that ‘some 25-60 million people are directly employed in the fashion industry…. Modern slavery, child labor, poverty, gender discrimination, and low pay are rife within the garment supply chain.’

Hopping on fleeting trends of any kind can be problematic because we can’t trace where our clothes come from, and by buying at the rate we do, we’re propping up damaging systems of oppression. So it’s better to buy mindfully – to buy things you’ll re-wear, and analyze why you want to wear something. Hint: if you’re trying to look cool by mimicking the homeless population, you probably should go back to the drawing board.


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