Justin Bieber arrived at the 2015 American Music Awards in one of the most conspicuous T-shirts ever made. Every inch of it was covered in imagery tied to “Heart-Shaped Box,” the first single off Nirvana’s 1993 album, In Utero. The all-over print featured black, red, and blue hearts of varying sizes; gold lettering; an actual heart-shaped box; lilies; and the In Utero album art.
Seeing the singer of “Baby” draped in the regalia of grunge’s most iconic band provoked some strong reactions. Nirvana’s most sensitive fans expressed utter disgust. Spin snarkily implied that the pop star was a poser with the headline: “Noted Grunge Fan Justin Bieber Wore a Nirvana T-Shirt to the AMAs.” And Courtney Love, Kurt Cobain’s widow, actually complimented the teen idol, tweeting, “You’re cool in my book.”
After the AMAs, graphic artist Bill Mooney was surprised to see news stories about Bieber’s Nirvana shirt. Scrolling through the photos was even more surreal. “It was a little strange,” Mooney says. Not because a massively popular, young artist wore an old band tee to make a fashion statement, but because of the particular tee he chose.
The founder and co-owner of the music merchandise company Tannis Root, Mooney came up with the “Heart-Shaped Box” shirt in 1993. At the time, it was not his favorite concept, and he admits that it still hasn’t really grown on him. “I don’t think I saw another one out in the wild for another 10 years,” Mooney says. “And at some point, I saw one and again thought, like, ‘God, that’s not a great-looking shirt.’”
Collectors, however, disagree. An original “Heart-Shaped Box” shirt, depending on condition and variant, can go for between $1,500 and $3,500. Rarer, more valuable Nirvana merch exists—like some Sub Pop–era tees—but there’s no single piece coveted more by the typical T-shirt head. “It’s the most culturally significant vintage shirt in the community,” says Joe LaMonica, co-owner of Faded, a vintage clothing collective that just staged its second annual convention. “I think it actually even translates over to the masses. Not my father, but young kids who see that shirt will recognize it, as opposed to an old shirt from a Nirvana limited run that they only printed 150 of.”
The story of the “Heart-Shaped Box” T-shirt is, on the surface at least, about how commodified nostalgia and celebrity hype turned a maximalist eyesore into a Holy Grail. But it’s also about the power of Nirvana. Since the release of its last studio record 30 years ago this month, the trio has transformed from a beloved short-lived band to a ubiquitous lifestyle brand. Modern Nirvana apparel is available at a wide range of prices in countless stores, from big-box chains like Walmart to far more expensive boutique retailers. People from all walks of life identify with it, whether or not they can name three Nirvana songs.
“A Nirvana shirt has a different meaning for you or me, where we have a lot of experience with the band’s music or grew up with them. And so that shirt is just kind of an icon or a portal to all that meaning,” Mooney says. “But when I see somebody wearing a shirt that says ‘Nirvana’ and has a smiley face on it, it can just operate on the level of that word and that goofy, blissed-out smiley face. It just works on a level of a slogan and a simple image.”
Nirvana was both subversive and accessible, which gave the band something extraordinarily rare: dual appeal. “Even when they were mainstream, as popular as they got, the music still had an edge to it that transcended the popularity,” says Rick Moe, a longtime vintage band T-shirt collector and dealer. “You can’t really say they sold out. At least I don’t. And then Kurt died and they stopped. [But] there was no fading out.”
Cobain was a punk-rock supernova, a mesmerizing explosion that burned so bright it left a permanent afterglow. He may be gone, but he still has a light—and the ubiquity of Nirvana tees in 2023 proves that. Dropping thousands of dollars on a “Heart-Shaped Box” shirt may seem ludicrous to most, but if you can afford one, there’s no bolder statement piece. A record collection is cool, but as Richard Colligan, the owner of Metropolis Vintage in New York City, once told me, “You can’t wear vinyl.”
Every new band T-shirt collector has to get over the sticker shock. Seven years ago, LaMonica walked into Metropolis in the East Village and was greeted by walls lined with rare music tees. After geeking out and finally managing to compose himself, he asked the salesperson to see one: a 1986 Cro-Mags shirt that featured artwork from the band’s first album.
The price tag said $900.
“I quickly told him to put it right back on the shelf where it belonged,” LaMonica says. At that moment, he realized two things: (1) His hobby might be a pretty expensive one, and (2) old T-shirts mean a lot to people. “Pieces of clothing that are attached to specific cultural importance do have different values,” he says. “And the values of those do fluctuate pretty significantly.”
Three decades after their moms and dads got rid of all of their ratty grunge T-shirts, Gen Xers and elder millennials can now buy back small chunks of their childhood for hundreds of dollars apiece. To my bank account’s detriment, I’ve spent the past 10 years piling up a brand-new stash of Nirvana, Soundgarden, Pearl Jam, Smashing Pumpkins, Hole, and Beastie Boys tees. Finding one on eBay that I’ve been looking for is a rush, even if I occasionally have to pay 15 or 20 times the original retail price for it. (I said occasionally, OK?)
These days, there’s nothing unique about my vintage habit. Secondhand clothing has become a hundred-billion-dollar business. That covers everything from sneakers to denim to militaria to workwear to streetwear to lingerie to dresses to bathing suits to snapback hats to jerseys.
High-end vintage pop culture tees are a small but, in recent years, prominent part of that world. In late 2020, when pandemic boredom and stimulus checks led vintage prices to skyrocket, a T-shirt covered in a giant print of Genie from Disney’s Aladdin sold on an Instagram livestream for $6,000. The next year, Sotheby’s auctioned off a 1967 Grateful Dead tee for, expenses and fees included, nearly $20,000. And this summer, the luxury fashion house Yves Saint Laurent released an astronomically priced, curated vintage Nirvana collection that features a $4,450 Incesticide shirt that you can find elsewhere for far, far less.
People have collected merch since the dawn of rock ’n’ roll, but the current market for it was seeded in the ’80s. Touring acts back then sold $15 to $20 T-shirts by the bushel, flooding America with the kind of stuff for which vintage sellers now scour thrift stores, yard sales, and rag houses. In 1987 alone, fans reportedly bought $300 million worth of pop music tees. With tons of money to be made, merchandisers started shelling out eight-figure sums for the right to produce T-shirts for the world’s biggest bands. In 1989, Brockum became the official apparel provider for the Rolling Stones’ Steel Wheels Tour—thanks to its parent company’s payment of $70 million.
In those days, Mooney wasn’t inking million-dollar deals. He was a teenager in Raleigh, North Carolina, who’d convinced his art teacher to let him do an independent study in screen printing. In the summer of 1985, not long after his high school graduation, one of his favorite bands came to town: Redd Kross. On a whim, he presented the members of the group with sample T-shirt designs—one was a photo of Madonna that had just appeared in Playboy. The band liked them. “We wound up printing their dirty laundry one night,” Mooney says. “T-shirts, white pants, basically anything that they wanted to. And they wound up wearing that stuff.”
Two years later, Redd Kross asked Mooney and his partners, Barbara Herring and Mike Carter, if they’d produce the band’s tour merch. “We just said, ‘OK.’ We didn’t have equipment,” Mooney says. “We just hand-placed the screens and did these really labor-intensive shirts that would be completely impractical to do if we didn’t have cheap rent and too much time on our hands.”
And that’s how Tannis Root was born. The fledgling company, named for a sinister substance used as a MacGuffin in Rosemary’s Baby, soon landed another indie band as a client. “Sonic Youth played Chapel Hill, and we took them some of the shirts we just made for Redd Kross, because we knew they were Redd Kross fans,” Mooney says. “They loved them and said, ‘Oh, well, we’ll be in touch.’”
The alt-rock icons, who shared a manager with Redd Kross, hired Tannis Root to make their shirts. Then, in the summer of 1989, with the company set to deliver merch to a Sonic Youth show in Manhattan, guitarist Thurston Moore called Mooney. “‘Oh, you should come up at least a day early to check out these Sub Pop bands that are playing,’” Mooney remembers him saying. One of those bands was Nirvana. “They were amazing,” Mooney says.
By then, Tannis Root had also started to make merch for Mudhoney. That December, the grunge pioneers played Lame Fest U.K. with fellow Seattle bands Nirvana and Tad. Mooney designed the shirt for the show. The front print is a photo of a naked woman that he found in a sex shop at the back of the South Carolina truck stop South of the Border. “Most of the porno was just these black-and-white booklets that were stapled together,” Mooney says. “That photo, she’s kind of wearing a mod biker’s cap and a scarf. And it looked more like Swinging London than it did a South Carolina truck stop.” The back print is slightly less risqué: just the names of the three bands in tongue-in-cheek stars-and-stripes block lettering. Today, the shirt is worth an absurd amount of money.
Mooney continued to cross paths with Nirvana. When the band stopped in Chapel Hill on the 1991 Nevermind tour, a roadie who was also Mooney’s friend asked him to make some shirts. The resulting black long-sleeve tees featured Nirvana’s smiley face logos and the names of each member of the band and crew. “I think I literally printed one for each member of the band and crew. So it was probably 12 total,” says Mooney, who has only one of the shirts today.
But Tannis Root didn’t officially collaborate with Nirvana until a few years later, after Cobain and Co. had shockingly become one of the biggest bands in the world. Brockum, whose roster included the Stones, Metallica, and Pink Floyd, had signed Nirvana, but it didn’t feel like a good fit. The band may have been huge, but it wasn’t playing grandiose stadium shows like the merchandiser’s other clients. “Nirvana was probably a point of pride to have but not the biggest moneymaker,” Mooney says. “And they honestly didn’t know what to do with it.”
Cobain was punk. He preferred a more … DIY aesthetic. “He was unhappy when he would send his artwork to them, the look of it when it would come back,” Mooney says. “Just because [Brockum’s] style was just those hair-metal band shirts and classic rock.”
The Nirvana frontman was familiar with Tannis Root. He was often seen wearing Sonic Youth T-shirts. So with the blessing of the band’s management, Mooney and Cobain talked about collaborating on a design for Brockum. Mooney recalls that their phone conversations made him slightly uncomfortable. “Courtney would be yelling in the background, and he would be kind of snapping back, like, ‘I’m talking on the phone. Can you just give me a minute?’” he says. “I remember calling my contact at the management company at the time, just saying, ‘I don’t know about this. That wasn’t a very fun vibe.’ And to their credit, the person at the merchandising company was just like, ‘Kurt wouldn’t be talking to you if he didn’t want to. And this is good for him to work on these designs, to try to hash it out creatively.’”
One of Mooney’s ideas for Cobain, who took a hands-on approach to everything related to Nirvana, was an image of a fish wrapped in tabloid articles about the band. “I did a sketch of that and sent it, and he really liked the idea,” Mooney says. The concept stalled when Cobain insisted on including a snippet from an infamous Vanity Fair article about his marriage. “It wasn’t a forum where you could really address all of that,” Mooney says. “So I just kind of backed off on it and never finished it.”
The calls never led to a workable idea, but after the In Utero tour started, Mooney heard from Nirvana’s management again. They said that Brockum had just bought a belt printer—an expensive piece of equipment that could produce oversized, multicolored, multilayered T-shirt designs—and wanted Mooney to come up with something that took advantage of the technology.
Nirvana’s record label, Geffen, had sent Mooney a disk full of art from In Utero. One of the images, of a pink, heart-shaped box flanked by lilies, appeared on the international single sleeve for “Heart-Shaped Box.” Mooney used that as the centerpiece of a new shirt design, which he created on his Mac. The color printout that Nirvana OK’d has a handwritten note by Mooney on it with a simple message: “Use this one.”
Soon, “Heart-Shaped Box” T-shirts were rolling off the presses and onto Hot Topic shelves across America. At the time, the design wasn’t a bestseller. Mooney still has no idea how many were printed, and Norman Perry, then-president of Brockum, remembers nothing about that particular tee. Brockum produced merch for only one Nirvana tour. It would be the band’s last.
In the years following Cobain’s crushing death at 27, grunge’s overall popularity gradually waned. Fewer and fewer teens wore Seattle band tees, which weren’t old or rare enough yet to be worth much. And by the end of the decade, current artists had started to swap out big and bold T-shirt graphics with more understated art.
When he was working as a buyer for SoHo vintage boutique What Goes Around Comes Around in the aughts, Moe never saw ’90s stuff on the racks. “Whether it’s rap tees or grunge or anything, just because it wasn’t, quote, unquote, old enough,” he says. “But it was what I was. I listened to that music. I went to those shows. So whenever I would find that stuff—and we’re talking about a time [when] you could find that stuff really cheaply, certainly compared to now—I would always grab it.”
In 2009, Kid Cudi came into the shop looking for music tees from his childhood. “I would always have a personal stash downstairs, a bag full of my own stuff I would sometimes sell,” Moe says. “He was one of the first clients I had that would buy into that. And if you have any client that’s buying in bulk, you start sourcing that same stuff.”
When Moe moved to Seattle in 2011 and later opened Tyranny + Mutation, he continued to pile up ’90s shirts. And despite his occasional non-buyer’s remorse—when offered 10 deadstock Pearl Jam T-shirts printed specifically for the “Alive” video shoot, he left thousands of dollars on the table by grabbing only one—Moe found his personal grunge gold mine in the Pacific Northwest. “It was like a dream,” he says. “I could source that stuff cheaply and plentifully there. … I could pull 100 tees, really good stuff, for a grand or two.”
Around the early 2010s, Moe noticed that the T-shirts he loved were creeping up in value. Then, fashion designer Jerry Lorenzo contacted him out of the blue. The founder of the streetwear label Fear of God was building a collection of the kind of tees Moe had amassed. “That was the exact stuff that he was buying,” Moe says. “A real similar vibe to what Kid Cudi was buying, but Jerry was going all out. He was buying 60, 80 T-shirts at a time. And back then, I could do that. I could source all of that stuff.”
One of the T-shirts Lorenzo snagged was a Heart-Shaped Box. Moe originally bought it for $75. The designer chopped the tee’s sleeves, added Fear of God branding in white ink to the front and back, and in 2015, put it on Justin Bieber’s shoulders.
All of a sudden, Moe’s customers wanted that gaudy Nirvana piece. “I couldn’t keep that shirt in stock,” he says. “And every one I saw, I would buy, and it was totally worth the money.” By early 2016, he recalls resale shops selling it for $400 or more. Before long, it was up to over $1,000. “Those four years, you’re just seeing prices on that stuff really go up incrementally by the hundreds,” Moe says.
With ’90s nostalgia’s crest in the 2020s, the demand for vintage band merch has continued to go up. The “Heart-Shaped Box” tee, now in some cases worth $2,000 or $3,000, is an extreme example of that. Because no two pre-owned tees are exactly alike, the Tannis Root design doesn’t have a single, universally accepted price. Before pricing or buying one, T-shirt nerds consider the condition (holes and other flaws), the wear (softness), the fade (print distressing), the size (an extra large is the most desirable), and the variant (the Canadian- and Australian-made versions are particularly coveted). But no matter what, any version of the Heart-Shaped Box is valuable.
So valuable that the shirt has become an object vintage shop owners show off to draw in discerning collectors. “It’s like a cornerstone piece,” says Ryan Haas, one of the co-owners of Faded. “I don’t really see many people who actually wear them.”
Adds Moe: “Nirvana fans or vintage dealers that wear Nirvana shirts, a lot of those people don’t like that shirt, or they would never wear it. It’s just too loud, and it’s a really heavy print. So a lot of times, unless it’s really worn out, it’s a heavy shirt to wear.”
There’s some irony in the fact that the ultimate Nirvana signifier has become something that’s kept behind glass like a museum artifact. The band came up in an alt-rock scene that rejected slick designs in favor of homegrown merch that kids actually liked to wear. And when he was alive, Cobain railed against the corporatization of rock. Now, his group’s T-shirts are part of a luxury industry.
Thirty years after designing the Heart-Shaped Box, Mooney isn’t terribly shocked that it’s now a collector’s item. What is surprising to him is how many different kinds of people he sees wearing modern, inexpensive Nirvana tees. In a way, it’s a fitting tribute to Cobain, a man who seemed to genuinely care about inclusivity. One specific T-shirt Mooney has noticed features a version of the band’s blissed-out smiley face that’s been rainbow colored. “I don’t know that that design would’ve ever been approved by Nirvana back in the day,” Mooney says, “but I’m sure that they appreciate more that the shirt is being worn, and not just by macho bros.”
By the time it worked with Nirvana, Tannis Root was no longer an underground shop. In 1995, it was making tees for almost half of the bands on Lollapalooza’s main stage. Today, the design firm is still known for its cool T-shirts through the work it’s done for bands like Pavement, the Avett Brothers, and Tame Impala.
Over Labor Day weekend, Faded featured an exhibit highlighting the work of Tannis Root. The company’s tees were displayed on the walls of the WaterFire Arts Center in Providence, Rhode Island, and, more meaningfully, on the backs of many of the thousands of vintage collectors flooding the event. “We’re really concerned with art and giving context to these things,” LaMonica says. “Because without that, they’re just pieces of clothing.”
That day, there were only a few “Heart-Shaped Box” T-shirts in the building. Mooney got rid of his long ago. “When it was all over, I got paid for it, and I probably had 10 or 12 of those shirts,” he says. “And I really did sell those at a yard sale.”
Mooney has no recollection of who bought them, but he knows it wasn’t any of his friends. “A lot of them were Nirvana fans who’d seen Nirvana play to 100 to 200 people in Chapel Hill,” he says. “And they probably weren’t that interested in them either.”