The Best Supreme Photo Tees

Each and every season, the latest Supreme photo tee is a moment: the rare item that can cut through the increasingly thick chaff of the social media-fueled, largely post-subcultural world of streetwear we find ourselves in. Since the brand first introduced the photo tee in 2005, it’s become a quintessential item and has featured everyone from rappers to heavyweight champions, supermodels and even a beloved Muppet on its chest. Though we’re not too far off from the 20th anniversary of the first photo tee — and even closer to Supreme’s 30th anniversary as a brand — the tees still continue to make noise, and the latest subject, NBA Youngboy, is no exception to that rule.

With all the buzz, both positive and negative, around Youngboy’s inclusion in the lineage and the forthcoming release of Supreme’s expansive Fall/Winter 2023 collection, Hypebeast has rounded up the nine best photo tees (plus one honorable mention) from the brand’s history and listed them in chronological order. Purists, take note: this list only contains Supreme’s signature portrait tees, meaning that other seminal designs like 2007’s Tera Patrick tee, 2011’s Prodigy tee and 2012’s Three 6 Mafia tee are not included.

Raekwon

Duke’s Archive

Year Released: 2005
Photographer: Kenneth Cappello

Wu-Tang Clan bruiser Raekwon the Chef was the subject of Supreme’s first-ever photo tee, shot by Kenneth Cappello in 2005. They say that you never forget your first love, and Raekwon’s photo tee is still held among the very best photo tees Supreme ever produced almost two full decades later. Why? Because it perfectly encapsulates the brand’s unique mixture of danger, attitude and playfulness. Raekwon wasn’t alone in his photo: he was accompanied by his machine pistol-toting, middle-finger-flipping pal Cappadonna and a denim overall-outfitted Tickle Me Elmo toy. Supreme had no web shop when this tee released, so it was available exclusively at the brand’s New York City, Los Angeles and Japan stores, at least until Disney caught wind of Elmo’s proximity to an automatic weapon on it and swiftly slapped Supreme with a cease-and-desist.

Diplomats

Duke’s Archive

Year Released: 2006
Photographer: Kenneth Cappello

Shot once again by Kenneth Cappello, the Diplomats photo tee with Jim Jones and Juelz Santana was a seminal moment in the brand’s history that bridged the worlds of skateboarding and hip-hop while also encapsulating the flash and attitude that was core to the Dipset lifestyle. Both Jones and Juelz were at their hottest too: Jones would drop Hustler’s P.O.M.E (Product of My Environment), spearheaded by “We Fly High,” still his biggest song to date, that year, while Juelz was fresh off the 2005 release of What the Game’s Been Missing!, which featured “There It Go (The Whistle Song).” The duo’s flamboyance was about as far removed from Raekwon’s sharp-edged ruggedness as imaginable, but there was one very important similarity: namely that both represented New York City in their own incomparable way. (On a side note, Cappello notes that the vibe of the shoot was weird with “a lot of ego,” as Jones wanted to be paid up front, and in 2018, Jones indicated that he felt Supreme owed him a piece of the company for his participation).

Mike Tyson

Duke’s Archive

Year Released: 2007
Photographer: Kenneth Cappello

For its third photo tee, Supreme took a break from photographing New York rappers and instead enlisted one of New York’s most famous brawlers, Brownsville native Iron Mike Tyson. Though the final professional fight of Tyson’s two-decade-long career had taken place two years earlier, the former heavyweight and light heavyweight champ still cut an imposing figure. Kenneth Cappello, back for his third photo tee in a row, went out to Las Vegas to photograph Iron Mike in his hotel room at a casino and recollects that Tyson was in a foul mood, spending most of the hours-long shoot grumbling, cursing and intentionally terrifying the photo assistants. That sharp, unfriendly energy is captured in the tee, which shows a no-nonsense Tyson leaning ever so slightly to his right, making for a nontraditional portrait and one of Supreme’s most memorable tees ever to boot.

Kermit the Frog

Duke’s Archive

Year Released: 2008
Photographer: Terry Richardson
Kermit the Frog is about as unintimidating as Tyson can be terrifying, and he touched down on a photo tee the year after Iron Mike The first tee shot by Terry Richardson, Kermit’s shirt was an officially licensed project with Jim Henson’s Muppets Workshop, a far cry from the unauthorized use of Elmo on Raekwon’s tee three years earlier. Kermit also didn’t keep that thang on him, instead opting for a custom-made tiny box logo t-shirt. To this day, Kermit is still the only puppet to be photographed for a Supreme T-shirt, and serves as one of Supreme’s earliest attempts to mend fences with an entity they’d ticked off — remember, this is a brand that was ceased and desisted by Louis Vuitton for Damier-inspired monogram skate decks in 2000 before their culture-shifting collaboration with the French fashion house in 2017, and created a “F*ck Nike” T-shirt in 2001 before working with Nike SB to create one of the most memorable SB Dunk collabs of all time in 2002.

Kate Moss

Duke’s Archive

Year Released: 2012
Photographer: Alasdair McLellan

By the time legendary British supermodel Kate Moss was tapped to appear on one of Supreme’s photo tees in 2012, she already had a rich history with the brand, having worked with them in 2004 on a 10th-anniversary tee for their NYC store, in 2006 for the “Kate Kiss” tee and in 2008 for a Daikanyama, Japan store 10th-anniversary tee in collaboration with KAWS’ Original Fake. Moss’ “Blue Steel”-level stare into photographer and fellow Brit Alasdair McLellan’s lens, the smoldering cigarette in her fingers and the bright pop of red on her box logo tee all stand in contrast to her striking leopard-print fur coat, making for a tee that perfectly encapsulates the cooler-than-cool attitude of brand and model alike.

Neil Young

Duke’s Archive

Year Released: 2015
Photographer: Terry Richardson

Music has been a key part of Supreme’s lineage since the day it first opened its doors on Lafayette Street. The brand has always dabbled with designs and subjects across genres, from hip-hop to jazz to reggae and electronic, so although Canadian singer-songwriter Neil Young may have seemed to be a strange choice to younger Supreme fans when he was spotlighted in the brand’s SS15 campaign, he was far from it as both brand and artist boast a fierce independent streak. Young, who was already in the Rock & Roll Hall of Fame when the tee came out posed in one of the brand’s famous box logos for Terry Richardson, portraying a mixture of toughness and elegance that, combined with that famous red rectangle, made for one of the very best photo tees of the 2010s, and served as a reminder that Supreme’s influences come from all over the cultural diaspora.

Morrissey

Stockx

Year Released: 2016
Photographer: Terry Richardson

Raekwon may have been cease-and-desisted, Dipset might have wanted a larger piece of the pie Mike Tyson may have been angry, but there’s no Supreme photo tee surrounded by more controversy than Morrissey’s. When the Smiths frontman-starring campaign for Supreme’s SS16 collection rolled out in February of that year, Morrissey took to his website to renounce it, saying that he didn’t like any of the photos that Terry Richardson shot, that, as a vegetarian, he wasn’t aware that Supreme had worked with the “beef sandwich pharaoh” White Castle, and that he’d issued the brand a “legal caution” to not use his photograph. Supreme, for their part, issued a long statement detailing the difficulty of working with the notoriously fickle singer and his unwillingness to come to an agreement, forcing them to release the tee to recoup the investment of their photoshoot. If you want to reminisce on the whole story you can do so here — it’s one of the zaniest stories from the brand’s history and prefaced Morrissey’s fall from pop culture grace in the following years as well.

Gucci Mane

Stockx

Year Released: 2016
Photographer: Harmony Korine

What do Gucci Mane and Supreme have in common? They’ve both worked with Harmony Korine. Korine and Supreme go all the way back to 1995, when employees and friends of the brand appeared in Kids, while Korine and Guwop worked on Spring Breakers in 2012. When Gucci was released from jail in May 2016, Korine visited him at his Atlanta mansion and shot a memorable video campaign, then, later in the year, the two’s photo tee dropped. It’s the first shirt on the list that features text on both its chest image as well as its back, but Supreme has bent the rules of what makes a “photo tee” again since then, and Gucci was at the peak of his post-prison powers in 2016.

Nas

Stockx

Year Released: 2017

April 1994 saw the birth of two seminal pieces of New York City — and by extension, global — street culture: Supreme opened its doors for the first time and Nas dropped his seminal debut album Illmatic. The LES and Nasty Nas’ Queensbridge home were only separated by a few miles, but the above-mentioned bridge between skateboarding and hip-hop hadn’t been in full yet, so the two became legends in their own spheres first before connecting for what felt like a long-overdue link-up in 2017. The second photo tee on this list to feature a text hit on its chest, the Supreme Nas photo tee is NYC through and through, an acknowledgment of the God MC’s sublime skill, the cultural haven that was 1994, and the two’s shared Big Apple roots.

Honorable Mention: Andre 3000

Stockx

Year Released: 2022
Photographer: Deana Lawson

Tremaine Emory took over as Supreme’s creative director in 2022, and one of his first big moments was a photo tee with the legendary Andre 3000. Shot by Deana Lawson, Three Stacks’ photo tee was a step in a bold new direction for the brand. The reclusive artist had no ties with Supreme beforehand, but his uncompromising creativity and willingness to do things his way, all the time, made for a paring that just felt right. The wheatpastes from the collection, put up around cities with Supreme stores, were a hot ticket item as well, ensuring that Emory’s tenure at the brand started with a bang.

For more from Supreme, check out the best Supreme x The North Face jackets.