How streetwear became stylish as luxury brands adopted a more casual approach

The lines between high-end and laid-back have blurred, making the aesthetic a pillar of the industry’s biggest houses

Skateboarding lifestyle brand Supreme is one of the leading names taking streetwear styles into the mainstream. Photo: Alamy

In 2020, at the height of the pandemic, I wrote an article about Justin Bieber’s Crocs collaboration and its ensuing impact. It wasn’t just Bieber, of course, the likes of Christopher Kane and Balenciaga had feted the plastic clog, too. But this felt like something of a tipping point for fashion and, let’s be honest, humanity at large (I may have dramatically used the word apocalypse). In my defence, I had been left alone with my thoughts under Covid-19’s stay-home rules for far too long.

However, the fact remains that a new strain of luxury fashion and streetwear had emerged from the chaos.

It wasn’t like streetwear hadn’t been on the radar of luxury brands for decades by this point. The big houses had noted its rise with interest on America’s east coast and the emergence of surf culture on the west. As the style dust kicked up and swirled, new brands such as Stuussy emerged in the 1980s. Shawn Stussy’s skatewear business operated on the limited-drop model that eventually proved vital for brands such as A Bathing Ape and Supreme.

While some luxury brands dabbled – Tommy Hilfiger and Ralph Lauren’s preppy look found its way onto the street some years later – it was the rise of hip-hop that was integral to building a bridge between these worlds. By the 2000s, Ye was dropping Gucci in his lyrics, while Jay-Z rapped entire bars about his Hublot watch collection.

“The initial attraction of luxury brands to the streetwear scene was driven by a strategic need to refresh brand image and connect with a younger, more dynamic consumer base,” says Kate Hardcastle, global consumer expert and chief executive of Insight with Passion.

But while there was indeed a merging of brands and culture going on, there remained a disconnect with the majority of this nascent audience – more often than not seeking a lower price point. So, while fashion houses recognised a need to reframe their future market strategy, if they couldn’t somehow reframe their affordability, too, then nothing else would really matter. Enter the luxury-streetwear collaboration. Toes had been dipped in waters, of course – Jil Sander collaborated with adidas in 1998 – but it wasn’t until midway through the 2000s that things started heating up in the collaboration game.

A$AP Rocky is an example of yuppiecore, sedate style with subtle flexes through expensive watches or jewellery. Getty Images

First it was through partnerships with similarly aligned brands such as Supreme x Vans, but eventually with luxury houses, too. Along came Fila x Fendi, Sẗussy x Dior, A Bathing Ape x Comme des Garçons, Supreme x Louis Vuitton and more. Then there was the zeitgeist attraction of the many “cores” – blokecore, Barbiecore, gorpcore, normcore, the list goes on.

These collaborations might not have come cheap – especially once they hit the resale market – but they proved much more attainable than high fashion items ever were. Supreme x Louis Vuitton was also interesting in that it, perhaps, signposted fashion’s new direction. In 2000, Louis Vuitton sent a cease and desist letter to Supreme, after it mashed up the brand’s famous logo with that of their own. Seventeen years later, the skate crew had become a conduit, of sorts, to Louis Vuitton’s future market relevance.

For Dubai fashion director and stylist Kate Hazell, the newfound entry point to luxury was vital. “I actually think that it’s such a democratic way of introducing luxury to a wider audience,” she says.

“With price points that are a little lower, a pair of sneakers, for example, is a more accessible and versatile way of buying into a luxury brand.”

As high-low collaborations brought fire to the industry, internal moves were also made. The luxury houses pumped out lines including football shirts, varsity jackets and hoodies while, in a seismic change of mindset, streetwear founders were actually sought out by the brands to take them forward. From the likes of A Bathing Ape founder Nigo at Kenzo to Virgil Abloh – and now Pharrell Williams – at Louis Vuitton, the game was turned completely upside down.

“The success of streetwear icons at the helm of high-end houses proved that there was a hunger for some fresh perspective,” says Sandra Yeghiazarian, founder of the Mena lifestyle platform, Yung. “The lines between streetwear and luxury had long since merged, creating a space for these designers to be comfortable in both worlds and help redefine luxury fashion for the future. This isn’t just a fad. Get ready to see more streetwear designers leading the charge at luxury houses, continuing to break down barriers and rewrite fashion’s rules.”

While I’m not obsessed with Bieber, (I’d like to make that clear), this feels like a good time to reference his latest luxury streetwear flex, namely a host of super-inflated XXL fits. Recently, he was seen wearing some oversized Balenciaga jogging bottoms and a pair of puffed-up Louis Vuitton fur boots.

Justin Bieber's latest luxury streetwear flex is mostly a host of super-inflated XXL fits. EPA

Bieber’s experimental outfits, in that respect, play more towards the wild lines of performative brands such as MSCHF, whose cartoonish Big Red Boots proved irresistible on social media last year, as they toyed with imaginative fashion both in the metaverse and real life. Now, that’s all well and good, but it does make it slightly disconcerting when trying to define what luxury actually means in 2024.

“[For me] it’s the craftsmanship, the attention to details, the materials used,” says Hazell. “The artisanal aspect of many luxury goods is what drives the price up. When it comes to a hoody from Balenciaga, however, I think it’s hard to justify the high price, other than that you’re paying for the name."

While you might assume that only the brands that have fully embraced streetwear have made it a central part of their business, the reality is actually more nuanced than that. “Is a T-shirt or denim considered streetwear?” continues Hazell. “I think both come under the broader streetwear umbrella, in which case I’d say it would be hard to find a luxury brand that has managed to survive in 2024 without introducing streetwear into their collections in some way.”

Streetwear has introduced a more relaxed approach to collection releases and has encouraged luxury brands to adopt a more fluid, responsive model of fashion presentation

Kate Hardcastle,
global consumer expert and chief executive of Insight with Passion

What’s certain is that streetwear is now seen as something of a core pillar of luxury in one way or another. Its parameters may shift, but its ethos remains embedded in the reworked DNA of the world’s fashion houses. “What started as a mere dalliance with streetwear has morphed into a foundational element for many luxury brands,” says Hardcastle.

“This isn’t just a passing phase; it’s a transformative shift in the fashion landscape. Streetwear has introduced a more relaxed approach to collection releases and has encouraged luxury brands to adopt a more fluid, responsive model of fashion presentation. This ongoing integration has influenced everything from design philosophy to marketing strategies, ensuring that streetwear remains a vital, vibrant part of the luxury fashion ecosystem.”

Speaking of the many lives of the luxury fashion ecosystem, you might recently have heard about yuppiecore (yes, another core). Here, more sedate style is the order of the day – shirts, ties, blazers – with subtle flexes that come by way of an expensive watch or some jewellery. Think A$AP Rocky’s recent outfits if you need a mental image. In the most meta way possible, that means we now have luxury houses embracing streetwear that imitates luxury houses. Get your head around that, and you realise fashion’s no-rules era remains a key marker for greatness.

“I believe streetwear’s success [in working with] luxury brands is all about freedom,” concludes Yeghiazarian. “It gives them a choice, it lets them ditch stuffy traditions while sifting through the brand’s core values, experiment with bold new designs and, most of all, reach new audiences. For customers, it’s the freedom to mix high-end with every day and express their own unique style. It’s win-win-win: luxury gets playful, streetwear gets new audiences and we all get more fashion freedom.”