It was just after 7pm on Wednesday, August 26, the opening night of Harry Styles’s Together, Together residency at Madison Square Garden, and a man in his 30s was haggling with a trio of young women outside the arena. Between them was a wagon overflowing with T-shirts in an assortment of colors.

“I’ll tell you what,” said the man with the wagon, who later introduced himself as Rob. “Let’s play rock, paper, scissors. If you win, it’s $50 for three; if I win, it’s $60.” Deal. “Rock, paper, scissors, shoot” — paper covers rock. Rob won. Three for $60. The women weren’t too upset about their loss, though. They’d already talked him down from $30 a shirt.

Scenes like this one played out all evening around the Garden, where Rob was one of more than a dozen entrepreneurial vendors who had gathered to sell Styles-themed apparel to concert-goers for a fraction of what it would cost for merch inside. None of these vendors had permission from Styles or Merch Traffic — the exclusive US licensing agent of the singer’s merchandise and a subsidiary of Live Nation — to produce and sell apparel featuring his brand.

In doing so, they were likely committing trademark infringement. And yet, this unlicensed, or bootleg, merchandise is a signature stitch in the fabric of fandom, one that fills an integral role in the live entertainment ecosystem.

“This is part of the experience, coming to the show, buying a shirt, going inside,” says Rob, who spoke on the condition that only his first name be used. “This is part of the fun.”

Bootleg merch is nothing new, but it is having a moment right now. In no place has that been more apparent than New York City, which this year hosted several major cultural events, such as Bruce Springsteen’s Land of Hope and Dreams tour in May, the New York Knicks’s NBA Finals run and the Fifa Men’s World Cup in the summer, and most recently, Styles’s 30-night residency, which runs through October 31.

The buzz has extended beyond the venues themselves. In almost every neighborhood of the city, you’re bound to bump into vendors who have set up shop near parks, subway stations, and bars looking to meet the fervent demand for soccer kits, Styles swag and Knicks gear.

Influencers have promoted the products on Instagram and TikTok, and fans are sharing information about where you can find the apparel in group chats. The result is a black market operating in plain sight.

The bootleg boom

Although there are occasional calls from companies like Merch Traffic to crack down on bootleg apparel, hardly anyone in position to do something about it seems to care. “We are definitively not enforcing it at the level that we used to,” says Robert Boland, a sports law professor at Seton Hall Law School.

There is no official data on the size of the unlicensed apparel industry because it is decentralized and unregulated; based on its proliferation alone, however, it appears to be thriving. The most obvious explanation for the bootleg boom is that there’s a massive market for merch right now.

Recognizing this, brands have opened new avenues to sell apparel to their fans beyond venues, flagship stores and the internet, most notably via pop-up shops. Offering exclusive merch and perks, these off-site auxiliary outlets have quickly morphed into their own marquee events for fans, who post about their hauls and the experience on social media, thus drawing additional attention to the products and enticing others to participate in the superfan economy.

Just scroll through TikTok and you’ll see the four to six-hour lines to get into Styles’s pop-up in Lower Manhattan.

On top of this attention-fueled demand spike, the apparel industry is still dealing with the supply chain hurdles that sprung up during Covid, says Boland. These supply issues, along with the high costs for companies to acquire licensing rights, have caused the prices of official merch to skyrocket.

The cheapest official Styles tour T-shirt costs $50, inside the Garden or at the Lower Manhattan pop-up shop, with the most expensive licensed clothes — Together, Together hoodies and the New York Harry Styles sports jersey — going for $85. The official New York Knicks Fanatics NBA Finals Champions men’s tees cost $65 at the NBA team store; the jerseys, $79.99.

The rising cost of these licenses has also led to the mass production of bland designs. “If you’re Nike, you don’t want to produce in multiple colors. You don’t want to produce in a bunch of different alignments,” Boland says. “You’re looking to make your product almost always for cheaper, because you’re paying a lot for the licensing.”

For the bootleggers, Boland says, “It’s really offered them a lane of creativity.” Or, as Bethany Murray, a 29-year-old woman who traveled from Washington D.C. for night one of Styles’s residency, puts it: “The bootleg designs are sometimes way cuter.”

Many street vendor bootleggers were hesitant to reveal specific revenue figures, but the ones who did say that, on average, they make a few hundred dollars a night. “If someone is doing this, their cost on the garment is no more than $5 a shirt if they’re buying them in bulk,” says Lindy Williams, the owner of Accent T-Shirts in Las Vegas, who has written about the bootleg merchandise industry.

So, if they have 100 shirts and sell them for $20 — a $15 markup — they’re turning a $1,500 profit. That’s a haul for the bootleggers, but it’s a relatively small amount for the brands themselves.

The creative surge

Murray was standing outside Madison Square Garden shortly before 5.30pm with her friend Kelly Ryan, also 29, who is from Boston. The two friends donned black ties bedazzled with beads spelling out Styles lyrics — “It’s New York baby always jacked up” for Murray; “My friends are in love with American girls” for Ryan — and multi-color, multi-shaped jewels.

“They tend to be more conservative about the official merch and try to make it neutral for everyone,” Ryan says. “I feel like the bootleggers can lean into a trend more, they’re like, ‘It didn’t cost us that much to make this, and we can just sell it for whatever and people are still going to buy it.’ I feel like a lot of it is the corporation of it all, trying to hedge their bets on what merch is going to be safe.”

Fortunately, for both the fans and the bootleggers, it has become easier and cheaper than ever for individuals to order quality custom clothing in bulk or to create their own. Armed with apparel, bootleggers took to the streets to cash in on Knicks Fever, while “providing a service that the marketplace was slow to provide,” Boland says.

Through that lens, brands might benefit from the bootleg boom — the possible losses of today could turn into profits tomorrow. That’s one reason why brands are not cracking down on street sellers, says Jodi Balsam, a professor of clinical law and director of the Sports Law Clinic at Brooklyn Law School.

On top of that, as Boland suggests, “the reason T-shirts are now [$50-65] at a concert venue or online is because they are pricing in for the knockoffs. I think the market has in turn priced in what they’re losing out on.”

The popularity of unlicensed apparel, though, is not just driven by convenience and affordability; consumers, especially younger ones, also find the anti-establishment ethos of bootleg merch appealing.

The cultural clout of the bootleg aesthetic was on display during the Knicks’s ticker-tape championship parade, when New York first lady Rama Duwaji, then 28, wore a custom dress featuring several upcycled bootleg T-shirts. The dress, as Vogue first reported, was designed by Miss Claire Sullivan, a 2026 CFDA/Vogue Fashion Fund finalist.

“My entire family is from New York, but have all since moved away, and everyone was texting me about wanting Knicks shirts,” Sullivan told Vogue in June. “I wasn’t able to go to any of the street vendors myself, so my friends helped me source.

When I saw how many colors there were, I was inspired to get one in every shade and turn them into a dress.”

Some brands, in response, “are co-opting the bootleg aesthetic,” Balsam says, noting that brands “are responding commercially rather than just legally. They try to collaborate with streetwear and fashion brands to make official merchandise feel more culturally authentic.” Others are following the Styles pop-up playbook and fully leaning into exclusivity — offering not just apparel, but also experiences that fans can’t get from the bootleggers.

“I like the exclusive merch they have here better than what they have at Madison Square Garden,” says Styles superfan Julie Prisco, a 27-year-old who lives in Midtown and has tickets to nine of the 30 residency shows.

It was a little after 3pm on Saturday, September 5, and she and her friend Ali Rimmer, who had come down from Saratoga for the show, had been waiting in line since 11am. Rimmer, 27, says that before she arrived, she expected the line would take about two hours; instead, it would probably take about two more hours just for them to get in.

They both agreed that waiting in the line for so long might not have been the most productive use of their time, but they wanted that free photo op and viewed the pop-up shop as part of the experience.

The two friends are perfect examples of how the licensed and unlicensed apparel industries can co-exist, supplementing and reinforcing one another within the greater merchandising ecosystem. “I feel like I’m going to get one or two things here,” Prisco says, referring to the pop-up shop. “I’ll never come back to this, because this is crazy. But will I also get merch at the concert? That could happen.”

She continues: “After the concert, I’ll get a bootleg for sure. They’re on every corner. Whenever you step out, they’re there. They get you on the high. You’re on the high of the concert, and you come out and are like, ‘I want something else.’”