By this point, Supreme is an immovable force. For over 25 years, the brand hasn't slowed on building and growing within the streetwear community, raising the bar even higher when it seems other brands are just catching up. The swiftness in which Supreme moves with cultural nuances is, in and of itself, a work of art. No other brand or institution has embodied streetwear's soul, starting out as a small spark on Lafayette Street that has grown so much it has spawned its own mini economy.

What started out with a re-appropriated logo on a T-shirt has since blossomed into over 25 years of covetable T-shirts, caps, outerwear, sneakers, and countless grails. Some more desired than others, but all with a message for their followers to decipher. That message was usually one word: Subvert. It wasn't easy to pick only a handful of highlights from the past two decades, but these are the best items Supreme has dropped since its 25th anniversary. 

1994: Original Box Logo T-Shirt 

And here is where it all begins. Released on opening day along with the Taxi Driver and "Afro Skater" T-shirts, we were introduced to the iconic box logo. Not even a logo, really. More of a symbol. Of status. Of cultural perception. Of the love for Supreme. It was also our introduction to Supreme's subtle takes on New York's historic and artistic culture, seeing as this icon was inspired by Barbara Kruger's work. Does Supreme even approach 25 years without this logo?

Honorable Mentions: Taxi Driver T-Shirt, Afro Skater T-Shirt

1995: Classic Logo T-Shirt 

Supreme's re-appropriation of Andre Courreges classic logo gave the new skate shop another version of its namesake on a T-shirt. This would clearly evolve into something bigger than the brand expected, as its small batch of T-shirts were beginning to sell out among all the neighborhood kids, including this very popular version, the origins of which few were privy.

1996: Supreme Vans Old Skool

 

Supreme was one of the first to build the bridge between streetwear and skatewear, taking a significant step in making the leap by creating its first collaborative shoe with the Vans Old Skool, which came in simple white, grey, and camo colorways. Along with a brand like Stüssy, these not only started what would be an ongoing and productive relationship, but played a serious force in spurring on the emergence and convergence of the skate- and streetwear genres. Fun fact: The first project Brendon Babenzien worked on when he was hired at Supreme in 1996 was to design colorways of Vans.  

1997: Supreme Camp Cap

Supreme wasn't the first to introduce them, but what can't be denied is the effect Supreme's camp caps have had on streetwear and the brand's counterparts. The box logo tee and camp cap pretty much go hand-in-hand in terms of historical reverence, all starting with the 1997 drop that included the leaf camouflage iteration.  It all took off from there. 

Honorable Mentions: Arabic Box Logo T-Shirt and the "Coca-Cola" Box Logo T-Shirt.

1998: Brooklyn Machine Works Bicycle

Cruiser bikes and skateboards are ubiquitous amongst the youth of NYC; how else are you gonna get from the LES to the West Village? Supreme's pulse to the street was apparent, but the limited release of this 24-inch cruiser bike, handmade by Brooklyn Machine Works, just solidified how in-tune to youth street culture they were. Only three dozen were made and sold, one of which was purchased by Eric Clapton, so unless you and Clap are homies, this will not be in your possession anytime soon.

Honorable Mentions: Keith Haring "Dog" T-Shirt, Original Houndstooth Camp Cap, and the Astronaut T-Shirt.

1999: Jackson Pollock Box Logo T-Shirt
 

The box logo T-shirt was slowly becoming the brand's Michelangelo-esque masterpiece with different iterations keeping the momentum going. But it was this Jackson Pollock version that may have started a revolution. It was apparent the brand liked to mix various aspects of culture, featuring re-appropriations of Warhol or the likeness of Basquiat on their tee. But using Pollock's "Number One" artwork within that tiny rectangular area begged the question; are they mocking or paying homage to the culture behind the piece? This was the subversive power of streetwear that pervaded the arena, with Supreme leading the way.

Honorable Mentions: Navy Box Logo T-shirt, "S" Five Panel Hat, and SSUR x Supreme T-shirts.

2000: Louis Vuitton Bootleg Skateboard Decks

Supreme had, and still has, no shame when it comes to re-appropriation—we see it in its designs every single season. But this notion didn't truly gain recognition until the brand took Louis Vuitton's famed monogram-print and stamped it on its skate decks, box logo T-shirts, beanies, stickers, and hats. The message Supreme was sending probably isn't as deep as one may think. But it symbolized its sneering rebellion towards the upper-class by throwing something as reputable as the LV monogram on a deck that was going to get scuffed to shit. Needless to say, LV didn't take much liking to this bite, resulting in the immediate removal and destruction of the remaining decks. So, if you managed to get your hands on one, you are sitting on a gold mine. 

Honorable Mentions: Ryan McGinness Pantone Skate Deck and Gucci Box Logo T-Shirt.

2001: KAWS Skateboard Deck

To this day, Supreme doubles as a gallery that exhibits the work of rising talents within contemporary art today. This KAWS’ skateboard deck is testament to how successful the brand’s art curation has always been. When KAWS made decks for Supreme in 2001, he was far from becoming a revered pop artist whose paintings now sell for over $14 million. Kudos to anyone who brought this KAWS deck and actually skated it. Although a set of these two decks recently sold for over $30,000, Supreme’s collaborative art decks weren’t exactly released with value in mind. According to KAWS’ interview with James Jebbia in the Supreme book, what was most important to Jebbia was “whose work will translate best onto a deck and mean something to our crowd and is not predictable.” 

Honorable Mentions: Jamil GS Calendar, Supreme x Padmore & Barnes M345 Sahara Boot, and Down Lows.

2002: Supreme x Nike SB Dunk Low

Even though the collaborations with Vans were hands-down successes, Supreme also understood the importance of Nike SBs to skaters and streetwear heads. Nike was a powerhouse on its own, but the emergence over the years of its skateboarding program is directly correlated to this Jordan-inspired Dunk Low. The iconic cement print paid homage to the Jordan I, which was hugely popular in the skating and streetwear world. Needless to say, these became a grail item in the culture that many have tried to recreate. Surprisingly, the collaboration only arrived after both brands briefly butted heads with each other. 

Honorable Mentions: Cement Camp Cap, Last Supper Skate Decks, and the Bathing Ape Box Logo.

2003: Supreme x Nike SB Dunk High

After one successful collaboration with Nike SB, why not do another? This time, the highly-covetable kicks in the form of a Dunk High featuring a faux croc print and metallic star print, which was utilized on other items to complement the shoes, including a beanie and a hoodie. The first release with Nike SB in 2002 caught everyone's attention, but this drop took the momentum to turbo speed.

Honorable Mentions: "Nuggets" Basketball Jersey and NWA T-Shirt. 

2004: Kate Moss T-Shirt

Back in 1995, Supreme crew members slapped a Supreme box logo sticker onto a Calvin Klein ad featuring the lovely Kate Moss. The squad was paying homage to the ad and placing their sticker on it as a form of respect. Calvin Klein didn't see it this way, and the company filed a lawsuit. Almost 10 years later, Supreme turned that whole situation on its head by releasing the ad, with the sticker, on a T-shirt, perfectly embodying the witty "zero fucks given" attitude that lies at the center of streetwear's collective mentality. 

Honorable Mentions: Andrei Molodkin "Fuck Bush" Skate Deck, Martha Cooper L/S Photo Series Shirt, and Vans Skate Hi SL.

2005: Rammellzee Backpack

Rammellzee was one of first artists to ever collaborate with Supreme and for good reason. A staple within New York City’s underground, he was a cultural icon that really didn't get the recognition he deserved. His original creations were visual crack. The limited backpacks the artist created for Supreme in 2005 is evidence of that. To find these one-of-a-kind graffitied bags, you'd have to pry from someone's cold dead hands. In the same year that saw the first photo series T-shirt with Kenneth Capello's "Raekwon" shoot and a Larry Clark collaboration, this bag definitely faced some tough competition. But the zeal that collectors have for it, and its classification as a true work of handpainted art, makes it the best item Supreme dropped that year.

Honorable Mentions: Raekwon Photo Series T-Shirt, Scatterweave Backpack, Harold Hunter Tank Top, and Larry Clark "Teenage Lust" T-Shirt.

2006: Supreme x Mitchell & Ness Baseball Jersey
 

A proper jersey will never die. That is why Supreme's subtle classic, created in conjunction with Mitchell & Ness, is a silent killer. Paying homage to the Brooklyn Dodgers' own Jackie Robinson with the number "42" on the back, Supreme entered the hall of the fame with this perfect replica of a jersey never made. Die-hard Supreme heads definitely have this at the top of their re-issue wishlists.

Honorable Mentions: Dipset Photo Series T-Shirt, Public Enemy x Vans Skate Hi, and Public Enemy Starter Jacket.

2007: Supreme x The North Face Summit Series Jacket

The North Face had established itself as a stylish status symbol, seen on everyone from middle-aged moms to corner-boys. A high-performance brand where fashion met function, Supreme realized what kind of clout the brand had behind its name ever since hip-hop embraced the outdoors label in the mid-'90s. The collaboration provided a more street-influenced option in the classic Summit Series jacket, featuring panels that weren't typically in The North Face's color palette and a lining one could only source from the streetwear brand. And while 2007 saw one of Supreme's best back-to-back collections, the original collab piece that started a legacy between the two is quite possibly the most powerful piece Supreme has dropped.

Honorable Mentions: Mike Tyson Photo T-shirt, Tiger Stripe Parka, and Oakley Sunglasses.

2008: Supreme Kermit Photo T-Shirt

Like the Box Logo, Supreme’s ongoing series of photo T-shirts is something that every looks forward to. The collection has shown love to an eclectic assortment of celebrities that each represent the brand’s “give no fucks” New York attitude in their own way. The list includes names like Mike Tyson, Dipset, Raekwon, and Morrissey. But one of the most coveted, and unexpected, photo T-shirts features one of the most famous puppets of all time, Kermit the Frog. Yes, the Muppets mainstay donned the BOGO back in 2008. Given Supreme’s mainstream popularity now it might make complete sense that this exists, but back in 2008 it was a monumental look for the at time controversial streetwear label to be officially represented by this beloved childhood icon. Scoring one of these T-shirts now cost you with some listings for as high as $1,000.—Mike DeStefano

Honorable Mentions: Visvim Camp Cap, Vans Leather Old Skool, Marilyn Minter Skate Deck, and The North Face Summit Series Skyline Jacket.

2009: Supreme x A.P.C. "Fuck 'Em" New Standard Denim

The mid- to late-2000s saw the peak of raw denim's rise. A.P.C., still the French denim brand du jour, was the go-to starter denim brand for everyone. From workwear aficionados to menswear enthusiasts, A.P.C provided the perfect introduction to raw denim by offering superior products. In interviews, James Jebbia has frequently mentioned that the French brand influenced Supreme. Definitely. I feel like A.P.C. has done a great job of really sticking to what they do. They keep an eye on what’s going on in fashion, but it’s always rooted in a ’60s kind of French style,” Jebbia told Interview Magazine. “Our stuff is pretty similar each season, but we keep an eye on what’s going on, and it’s always fresh, and there’s always, I think, a sense of the early ’90s to it.”  It was only a matter of time until both brands collided with this stellar collaboration in 2009. The collection featured a special embroidered pair of A.P.C.’s New Standard denim and a T-shirt. Very few pairs of these jeans have surfaced on the resale market today, and you’ll be lucky to find one with the “Fuck Em!” pin still intact. 

Honorable Mentions: WTAPS Award Varsity Jacket, Damien Hirst Skate Deck, and Ventile Jacket.

2010: "Supreme" Rizzoli Book

Prior to 2010, you could only piece together Supreme's storied history through scattered interviews, lore told outside the shop, and archived articles that popped up in forums. However, that all changed with the release of the Supreme book by Rizzoli, which compiled what are probably the greatest streetwear stories ever told. Unreleased photos never seen by the public? A product index featuring pieces that brand enthusiasts will likely never get their hands on? Now anyone could familiarize themselves with the near-mythical label just by studying the pages front to back. 

Honorable Mentions:  Motion Parka, Nunchucks, and Thunderbird Jersey

2011: Supreme x The North Face Leopard Nuptse Down Jacket

Supreme’s 12-year relationship with The North Face has resulted in plenty of impressive collections over the years. But few are as coveted, and out there, as the Leopard Nuptse jackets that released as part of their Fall/Winter 2011 collab. The Nuptse bubble coat is already established as a winter staple among New Yorkers in its classic, non-collaborative form. So adding leopard print (in gold, green, and grey colorways) and a black Supreme Box Logo to the right sleeve is of course going to have people going crazy. Drake rocked the grey version in the official video for “The Motto” that same year, which led to a whole new crowd on search of the item. It wasn’t the first time Supreme got a mainstream look, and it certainly wasn’t the last, but it’s just another reason why this jacket has remained so coveted almost a decade after its release.—Mike DeStefano

 Honorable Mentions: Playboy Varsity Jacket, Adam Kimmel Suit, Vans Chukka, Schott Perfecto Jacket, and KAWS Box Logo.

2012: Supreme Tree Camo Field Pullover

 

This particular outerwear piece from Supreme’s Fall/Winter 2012 lineup is already a fire statement piece on its own. Add a cosign from Kanye West and it becomes an all-time grail for plenty of Supreme (and Ye) fans. The field pullover came in olive green and safety orange options. Each is covered in brown tree camouflage and is finished off with an American flag embroidered on the left sleeve. Supreme is good for a handful of outerwear bangers every season, but that illustrious Kanye moment at the Céline Spring 2013 runway show notches this one ever so slightly above a lot of them.—Mike DeStefano

Honorable Mentions: Bengal Football Top, Snake Belted Shorts, Floral Pullover, and Levi’s Leopard-Lined Trucker Jacket

2013: Supreme x Comme des Garçons SHIRT Coaches Jacket

Comme des Garçons introduced the polka dot design for Supreme in 2012 for fanboys to go gaga over, but they really upped the ante by going full turbo on the brand's classic coaches jacket, mixing patterns in only the most brash and in-your-face of fashions. Blue and grey digi-camo with red dots and reversed Supreme logo became the go-to, must-have pattern for the year and it didn't hurt that it was introduced by cultural legends Jason Dill and Chloe Sevigny. 

Honorable Mentions: Taped Seam Fishtail Jacket, Supreme x Champion Satin Jacket, Fuck Denim Jacket, Schminx Coaches Jacket, and Vans ‘Power, Corruption, Lies' sneaker.

2014: "Cherry" Skate Video

As if to silence all the naysayers and doubters who believe Supreme’s relationship with skating had all but diminished, 2014’s “Cherry” came like a thief in the night (like all Supreme drops) and firmly cemented the brand’s place in the Thrasher pantheon. Directed by Bill Strobeck, Supreme’s first skate video reconciled its past (Jason Dill, Mark Gonzalez, Eric Koston) with its future (Alex Olson, Tyshawn Jones, Dylan Rieder). The brand's demeanor has always been aligned with the outsider appeal and grittiness of skateboarding, where style isn’t just a way of expressing who you are—it’s how you carve your lane in the streets with tré flips, no complies, and ghetto birds.

Honorable Mentions: Comme des Garçon Reversible Baseball Jersey, Supreme x Nike Foamposite, Taxi Driver Skate Deck

2015: Supreme x Air Jordan V

Like the infamous Air Foamposite One the year before, the Supreme x Air Jordan collaboration was monumental for the brand. Sure, working with Nike was nothing new for them at this point. But did anyone ever think that Supreme, a skate brand at heart, would get to remix an Air Jordan? Seeing the brand partner with a name as illustrious as Michael Jordan, that had absolutely no ties to skateboarding, further cemented just how much Supreme was becoming recognized in the mainstream consciousness. It was no longer just that cool brand that you saw being worn around SoHo in New York City and Fairfax Avenue in Los Angeles, it was hitting a new peak that would be fully realized two years later (more on that later).

The entire capsule is memorable, especially the lookbook shot of Michael Jordan himself sporting the Supreme x Air Jordan logo T-shirt. Three colorways of the V released. Two of them appeared more traditional with black nubuck and white leather uppers, respectively, but the highlight is easily the desert camouflage version. It’s like nothing we had seen dress the V prior to that moment. It showed that the Jordan brand gave Supreme the freedom to put its own spin on such a heralded model.—Mike DeStefano

Honorable Mentions: Comme des Garçons SHIRT hoodie, New York Yankees x ‘47 Brand Leather Varsity Jacket, Box Logo Crewneck, Crowbar, All-Star Basketball Jersey, and KIDS 20th Anniversary Collection.

2016: Supreme x Steep Tech 

By 2016, there had already been a number of Supreme x The North Face collaborations. The classic North Face Mountain Jacket arrived in a number of iterations that included reflective 3M, waxed cotton, and corduroy models. And the ever-popular Nuptse jacket arrived in many unique colorways that truly established the hype for Supreme’s collaborations with the heritage outwear brand. 

But when it came to releasing coats that truly threw it back to the ‘90s New York-era Supreme was rooted in, there wasn’t really much during those first nine years. Granted, there was a Supreme North Face jacket that featured a reflective flag patch, but it was nothing close to the Trans-Antarctica pieces that New York City heads drooled over during the brand’s heyday in the ‘90s. Supreme’s Steep Tech collection was truly the first North Face collaboration that tipped its hat to the New York City graffiti writers and boosters who popularized these jackets during the ‘90s. Back then, the Steep Tech Work Jacket was the cream of the crop, and Supreme’s new school version truly did it justice. The hoodies, sweatpants, and backpacks were also revivals of some of the skiwear line’s greatest hits. Since then, The North Face and Supreme have continued retroing the greatest hits from The North Face’s golden era. Everything from the brand’s rare Cordura Plus line to RTG gear.—Lei Takanashi

Honorable Mentions: Gucci Mane Photo T-Shirt, Morrissey Photo T-Shirt, Supreme “Pelle Pele,” Patchwork Anorak, Blade TC5 Collaboration, and the Supreme Brick.

2017: Supreme x Louis Vuitton Jacquard Denim N-3B Parka

Back in 2000, Supreme did what many streetwear brands traditionally do and decided to flip Louis Vuitton’s iconic monogram print and place it on skate decks. The storied French fashion house wasn’t feeling it and hit them with a cease and desist letter. At the time, the worlds of luxury fashion and streetwear could not have felt further apart. But 17 years later, the landscape was much different. The two were intersecting like they never had before. Still, an official collection between Supreme and Louis Vuitton would be the last thing anyone expected. 

But it happened. While then-men’s artistic director of Louis Vuitton Kim Jones has made a habit of fusing his love for streetwear with luxury throughout his career, LV’s CEO and Chairman Michael Burke is actually the one who pitched him on the partnership. The collection debuted in January 2017 at LV’s Fall/Winter 2017 presentation at Paris Fashion Week. The June release of the extensive capsule was limited with items like a $65,000 red monogram trunk or red monogram Box Logo hoodie earmarked as hot commodities. But there’s something about the jacquard denim parka, which is just understated enough despite also being covered in a co-branded monogram print, that stands above other pieces. If you were lucky enough to afford something from this collection, this piece is probably the best investment if factoring in wearability. —Mike DeStefano

Honorable Mentions: Faux Fur Bomber Jacket, Cowboy Denim Work Jacket, Sade T-shirt, MTA Metrocard, Scarface Hoodie, Obama Anorak, Fender Stratocaster, and Artek Aalto Tank 400 Chair.

2018: Comme des Garçons SHIRT x Supreme Chore Jacket

Since launching their relationship with Comme des Garçons SHIRT in 2012, these two great fashion brands have frequently joined together for one mission. To elevate the shirt. This was CdG SHIRT’s mission since it was first launched by Rei Kawakubo in 1988. Twenty-four years later, one of the greatest T-shirt companies of all time entered the picture. The most popular releases from Supreme’s collaborations with CdG SHIRT, are typically pieces that twist up the brand’s iconic box logo—the mirror, split, and crinkled box logo have all become hypebeast classics. But when it came to tapping into the essence of New York culture that Supreme is known for, there was just the Harold Hunter CdG SHIRT collection before this stellar release in 2018. 

Supreme has always cosigned New York City graffiti culture—getting JA One to draw a logo for the brand in 2008 is an impressive flex by itself. But no one expected New York’s underground graffiti scene to collide with the haute world of Comme des Garçons until Supreme made that happen in 2018. The brand printed Earsnot of the IRAK graffiti crew’s killer handstyle on Chore Coats, zip-up shirts, and Schott Perfecto jackets for their CdG Shirt collaboration. “For that collaboration, they asked me to rewrite something that was inside a blackbook I gave them. I was super blown away and I couldn't believe it,” Earsnot told Complex. “I thought it looked amazing and they did a great job with it.” There is nothing that defines New York City culture more than the graffiti seen on its streets. And the “Justice For All” tags on the jacket is a message anyone can get behind for years to come. —Lei Takanashi

Honorable Mentions: Lee Quinones collaboration, Public Enemy x Undercover, The North Face Cordura Plus, Mike Kelley, Steiff Bear, and Rimowa Suitcases.

2019: Swarovski 25th Anniversary Box Logo Hoodie

By 2019, Supreme was a much different brand than it was during its humble beginnings as a small skate shop housed on Lafayette Street in 1994. It had officially worked with Louis Vuitton. It had been valued at $1 billion. James Jebbia has a CFDA Menswear Designer of the Year award to his name. And its red Box Logo has become one of the most recognizable marks in fashion. So it makes sense that to celebrate its 25th anniversary Supreme had to add a luxury touch to its Box Logo T-shirt and hoodie. That twist came by way of crafting the logo out of hand-placed Swarovski crystals. The luxurious twist was just enough to give the design a new meaning, while staying true to the brand’s roots. Owning a Box Logo is already a status symbol within the streetwear community. So what’s an even crazier flex? Walking around with 1,161 (or 1,201 if you own the hoodie) crystals on your chest of course.—Mike DeStefano 

Honorable Mentions: Jean Paul Gaultier collection, Team Varsity Jacket, Reversible Patchwork Quilted Jacket, Apple Hoodie, Drum Set, Meissen Hand-Painted Porcelain Cupid Figurine, and Vol. 2 Book.

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