The 50 Greatest Streetwear T-Shirts of All Time

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Era: Streetwear B.C.

"This is a crazy massive one for sure. Bobbito and Strech Armstrong had the best hip-hop radio show of all-time. WKCR89 Tec9, best hip-hop radio show of all time. They asked PNB Nation to do a T-shirt for them. The T-shirt is one of the most important tees in my world because the radio show was so important, and PNB was so important. I was interning at PNB, and this shirt just means so much to me. It’s a very simple type shirt. The front just says "Strech Armstrong and Bobbito." It has the time, it says "89.9 Thursdays 1-5 a.m." And then on the back really big it said "89 Tec9," which was the name of the show.

"I remember when Staple hit its tenth anniversary. and we had our tenth anniversary event in New York where it was a big event. We had Lupe Fiasco perform, Clark Kent DJ'd, and it was a big thing. I was wearing a suit, I was sort of wearing nice clothes 'cause it was our tenth anniversary. But underneath my suit I was wearing the "89 Tec9" PNB Nation T-shirt, unbeknownst to everyone.  But to me it was important to wear that shirt because of how important that particular shirt was to the existence of my brand."

Era: Streetwear B.C.

"I mean this was such an important tee to me because it was in the very early days of starting my brand Staple and having the opportunity to work with Mos Def and Kweli on the shirt. It was just a massive honor."

Era: Streetwear B.C.

"This was done in a time, once again, pre category of streetwear—it wasn’t streetwear yet—but there was a time when raves were really big. Rave culture was really big and part of rave culture was T-shirts that were logo flips from major brands. 

"This was just representative of a time where logo flips were cool. The basis behind this was interesting because it goes deeper than just the logo flip. It was really young untrained designers getting their chops wet in design programs. That’s the real importance of this. So, whoever did this design, it would involve you first finding, shooting, or scanning a Wilson ball logo. Then you'd have to now take that and do your Photoshop, Illustrator magic and vectorize it. Then remove the 'W,' make the 'I' clean, add an 'L,' you know. So the need to make fun of a brand was the impetus for us learning technical skills almost like at a vocational school."

So instead of going to APEX tech or Devry Institute and learning Illustrator, we did it because we wanted to look cool at a rave. Regardless, the end result is that kids like Aaron from Milkcrate, Scott from 10.Deep, myself, Russ from SSUR, learned and got our chops on design programs by having this need to flip on major logos. That’s why this represents such an important moment in street fashion.

Era: Streetwear B.C.

"This Stussy tee, which in many people’s opinion is the grandfather of American streetwear. It's sort of the forbearer of it. A lot of young people don’t even know that Stussy is an actual person. But there’s a gentleman by the name of Sean Stussy who crafted surfboards, and he still does that to this day. He would just tag those surfboards with this tag that is sort of such a staple now. He made tees just to complement his surfboard business.

"Those hand-made tees in the beginning were what spawned streetwear. When he was doing it some 35 years ago, there was no street culture per se. It was just surf, and hip-hop was just beginning. I mean can you imagine that, just saying that hip-hop was just beginning? Its crazy! But hip-hop was just beginning, surf was there, and punk was there, which I believe was one of Sean's direct infelunces. So this is really where it all began, it's crazy."

Era: Streetwear B.C.

"This is one of those tees I still have that is way too gargantuan to ever wear, but I will never throw this T-shirt away. This shirt marked an Olympic moment during the Black Panther era of U.S. history. The fastest man who was predicted to win the gold medal in track and field was a Black Panther. The U.S. government knew that, and they were like. "Listen, we know you're probably gonna win and when you stand up and accept the medal, just be a good boy and just accept the fucking medal and just let the national anthem play and have a nice day, don’t do nothing crazy. We know you’re a Black Panther but don’t do anything crazy.'

"The story goes that as the national anthem plays he sort of looked down at his hands, which you can see in the first scene. There was just a struggle within himself as to what to do 'cause he was so against American politics—he was a Panther. Then, just as the song ended he put on a black glove and pumped his black fist in the air. On the world stage. I think they might have revoked his gold medal.

"PNB re-enacted this in a very beautiful way, very artistically done in my opinion in a nice subtle way. The text is so key in this design. Under the first one they put 'Intention.' And then on the last one they put 'Deed.' It's so powerful because the intention is that you’re a Black Panther and you have this mindset in your head. But if you're sharing in the glory and people are throwing enough accolades and medals at you, will you have enough within you to go through with the deed, the action.

"Almost like actions speak louder than words in a sense. It's like, 'Yeah, your intention is that you’re a Black Panther but do you have the balls to do it? Then the last scene is deed. It’s a fucking T-shirt design, that is heavy shit! That is volumes of information that, if you’re a young kid and you want to look this up, and this is before wikapedia so I would spend months going and see microfiche film at a library trying to find headlines and shit, all from a T-shirt. It's such a powerful medium."

Era: Streetwear B.C.

"One of the roots of street culture or street fashion is urban fashion. If you look at the heavy hitters today, like The Hundreds or the Diamond, their predecessors were Pelle Pelle, Roc-a-Wear, and Sean John. And Wu Wear was the predecessor to that. Sean John and Roc-a-Wear were brands started by rappers that were on a really major level, like they had shop-in-shops in Macy's, and they had runway shows. But Wu was really a clothing brand started by rappers and kind of operated by rappers, not by a garmento backer that was licensing the image. You really got the feeling that is was six childhood friends opening a store in Staten Island, and printing tees and making really weird fashion that basically only the Wu could come up with. There is something real genius about that.

"The fact that unfortunately it didn't survive the times because it didn’t have that experienced apparel maker background, but it was dope and it was very important I think in urban fashion and then leading into street fashion. And interestingly enough how now I think they have a deal of a partnership deal with Rocksmith to do the Tang apparel. It’s interesting now that the underdog from way back when is still today 25 years later some would argue is more relevant than the heavy hitters of back then. In some weird way Wu Tang won in the long run. They outlasted Roc-a-Wear and Sean John in terms of relevancy in my opinion."

Era: Streetwear B.C.

"This is one those designs that exemplifies the vibe PNB was on. The three names are all fatal victims of police shootings—Done on a 'HELLO MY NAME IS' sticker. It's just so raw, chilling and in your face—but at the same time, not grotesque. It's still 'designed.'

"This to me is genius-level street art. It's what streetwear should strive to be: visually compelling and conceptually riveting. The best advice Brue, the founder of PNB, ever said to me was, 'I don't care if you love it or if you hate it, as long as it provokes thought, I have succeeded.'"

Era: Streetwear B.C.

"Project Dragon was one of the smaller brands that I discovered at Union in SoHo. And I think Stash had Subware, that was his main brand. Stash is like a serial entrepreneur, I guess, because he had another brand called BFS, which was Blue the graffiti artist—rest in peace—Futura and Stash, which was a dope brand. BFS often referenced a lot of subway iconography. Subware was very graffiti-centric, so it had a lot of wild style graffiti type shirts.

"I think Project Dragon was Stash and Futura only. And Project Dragon to me was the most highly designed streetwear, and took influences from Japan. Stash used to go to Japan a lot because of the success of Subware. But it was a much more edgier, cleaner, more sophisticated streetwear line. Most prints were really small, He’d do a shirt with four point copy on it and call it a day and that was it. I was a graphic design major at school, and I loved the sensibility that he put into Project Dragon. Out of Subware, BFS, and Project dragon, PD was always my favorite one."

Era: Streetwear B.C.

"This was part of a series that they did that was just genius. They made a team for all the New York City boroughs with uptown meaning the Bronx. I know they had Brooklyn Roots as another team. Queens Kings was the other one. And Manhattan... Damn I forgot the other two. They made whole kits. These guys did the logo, did the identity, did T-shirts, tank tops and basketball jerseys, basketball shorts, backpacks, the cinch-top knapsacks.

"They did the whole nine. I think they even sponsored tournaments and stuff. It was really quite a thing that they created with this mock league concept. I just always loved this whole concept. They made a whole mock franchise, without the help of a million dollar company."

Era: Streetwear B.C.

"I've always loved Aaron and what he does with his brand and how he was able to survive the times and he’s still doing it to this day, still using the same logo. I really just wanted to include this because of the power of the logo and how it’s been able to stand the test of time,. It’s not a simple logo, he's never changed it. You would argue that it's not a simple logo. You look at this versus a Supreme box log and it's totally different. This is so handcrafted and cut and paste-y. 

"There’s so many things going on in this logo and this logo outlived the thing that it’s referencing. Vinyl records and milkcrates are long dead and gone but yet the logo has survived which kind of shows how strong his brand is."

Era: Streetwear B.C.

"Any Triple 5 Soul shirt is fine, just because of what the brand meant. Probably one of the first success stories from the business standpoint of streetwear. Probably one of the first streetwear brands to cross the $10 million mark, in terms of annual sales. Triple 5 Soul was the first store that ever bought a Staple shirt. The Triple 5 Soul store was a multi-brand store, and it was my first ever order—12 pieces of Staple shirts to Triple 5 Soul.

"Camella, who is the founder of Triple Five was always really supportive of Staple, and Staple would not be where it is today if it wasn’t for her. Not only did her store place the first order, but back when I used to go to Magic, the trade show, with just a backpack full of tees, no booth, just literally samples in a backpack. I was just hoping to stop someone in the hallway, and throw my shirts on the floor, and show them my shirts and hope to get an order. That’s how I started, but Camella pulled me to the side and was like, 'Yo, we have this booth,' and she said. 'We have some empty space, if you want just hang your shirts up here and you can do sales out of our booth.'

"She did that and that was so amazing. We got a little corner of the Triple 5 Soul booth and got great exposure out of that. Triple 5 Soul was such an important brand to streetwear. Sad that it’s not around anymore."

Era: Streetwear B.C.

"I was interning at PNB when this shirt came out. And alongside Stussy, which is sort of the West Coast grandfather of streetwear, I think PNB was the East Coast grandfather of streetwear. PNB always put a high level of thought in everything they did, way more than Stussy. Stussy was a great, very unique tag, had a great story, they had their Stussy global tribe they were able to get their name out that way. But Stussy didn’t really say that much. It was moreso cool and visually interesting.

"PNB was like the Cornel West of streetwear. Every shirt was an encyclopedia of knowledge, and so dope. This is just one of them: the 'Don’t Test' graphic. I think about this shirt all the time even to this day. It's just a big gun all photo copied, then splattered in execution and in small type underneat, just 'Don’t Test.' Don’t fuck with me. An awesome, passive-aggressive design. Not aggressive like the Rouge Status shirt or a Fuct shirt. Just subtle, sort of Malcolm X-style thinking just saying, 'Don't fuck with me, man.'

"So the back had a big red gun with 'Don’t Test' on it. The front of the shirt was a line drawning of a karate guy doing a crane kick. It looked like a diagram of how to do martial arts or kung fu and the back was a gun that said 'Don’t Test.' The mix of those two—ancient martial arts and street protection—don’t test either of them."

Era: Streetwear B.C.

"If you look at streetwear today, there's this whole category of clothing with aggressive curse words, or references to immoral acts. Whether it's naked chicks or weed leaves or curse words or pussy or whatever, there’s so many different vulgarities on shirts. It’s such a prevalent category today but back in the early-'90s, when Eric [Brunetti] formed this company, it just had this simple word on the shirt spelled slightly wrong so he wasn’t cursing, and it was genius.

"This was that shirt that as a youngster, you specifically wore this to the dinner table with your family so you would get yelled at. But then your rebuttal is that this isn't a curse word. 'F-U-C-T. I'm not cursing!' Then the parents would be like, 'Go to your fucking room!' It’s just being a smart-ass rebel, so simple and he encapsulated it very smartly. I think in my opinion, much smarter than the way people do it today."

Era: Streetweare B.C.

"Shepard [Fairey] came from the West Coast so this as a shirt wasn’t really that prevalent out in New York. It was more so the pastings and the stickering that infiltrated New York City. The clothing was really much bigger in Cali than it was in New York City.

"I wanted to include this just because of his hustle and how he was able to get his brand all around the world without any sort of marketing campaign, not with any advertising, not with celebrity sponsorship. He literally just traveled the world and put up his logo every single place that you could possibly imagine and that’s how he did it. So definitely the long, hard road but he did it nonetheless and you talk about timelessness, this is definitely one of the most timeless images that we have in street culture."

Era: Streetwear B.C.

"There's a lot of PNB on this list but I think it's well deserved. Proud Nubian Brothers was great because it was such a weird shirt. It's definitely something that you would think only a black person should be able to wear. But a lot of non-black people were wearing this shirt in the early-'90’s. And it was kind of okay and I don’t know why per se.

"I think that says something about streeetwear and how it was all-inclusive for everyone. That was the beauty of streetwear. Urban wear was for black people, skate wear was for white kids. Streetwear was the melting pot of all of them, where everyone was accepted. This PNB shirt, which was Proud Nubian Brothers, had the NBA Jerry West logo but with an afro and he had a halo over his head.

"It was just okay for everyone to wear, and I think that really helped instill that breaking down of color lines for people. I don’t know anyone that ever got called out for wearing that shirt even if you weren’t black, even if you weren’t a Proud Nubian brother. It just shows that you supported the cause. It was pretty cool."

Era: Streetwear B.C.

"For me this era was the height of what Phat Farm was, from the design and apparel standpoint. In the early-'90s the Phatfarm store in SoHo was a must-stop. You had to go there every weekend. It’s crazy where a brand can go. Now you would never imagine even touching Phat Farm, unfortunately. But in that sense it was a ahub of culture.

"I don't even see it in small towns. I go to middle America and I don’t see Phat Farm, I don’t know who wears it now. It's strange. You go to middle America and you see people wearing Affliction and Ed Hardy. I don’t see Phat Farm anymore, it’s strange."

Era: Streetwear B.C.

"Skate companies tried to be progressively more and more simple and create designs that stand a test of time. There’s probably no better example of that on this list than this shirt right here. They have just become the mark by which all other brands aspire to be and which I often tell young people, no brand will ever be again.

"James Jebbia has set the bar for what a brand should be, and everyone wants to be that but no one will ever be able to recreate what James did. It was a pocket, it was a moment of time, with the right people, the right elements, the right environmental things happening in New York City. I would even argue that James himself would not be able to recreate what Supreme has become. It’s a phenomenon."

Era: The Wonder Years

"Charizmatik was a brand that came up alongside Staple in the early-'90s. At this point, there was a gang of us that came up the same time. We were actually pretty close—it was like 10.Deep, Milkcrate, Charizmatik, Double Down, myself. We were somewhat the core of it but we all kind of started in the same year in the mid '90s and we were all of the same philosophy, same mindset.

"Zen, the name of the founder of Charizmatik, if I had to put a bet down back then was, in my opinoion, the most likely to succeed out of all of us. It’s ironic that he’s the one out of all of us that was the first to disappear as a brand.

"I just thought he had the most intellect and the most high-level thinking and best execution and his brand was just so straight on strong. He had all these hidden message labels inside of shirts. Every shirt had a different lining and he was charging a lot of money for his stuff, like $50 retail. Every shirt had like multiple levels of thinking and I just thought that man this is going to be it! Charizmatik is killing all of us! It's so much better than Staple, so much better than 10.Deep.

"I think Charizmatik not succeeding is a testament to someone who has too beautiful of a mind. In order to survive in this business, in any business, but specifically fashion and apparel, you kind of have to have a balance of a creative mind and a business mind. If you’re a true, true artist, you can’t really be successful in fashion because there’s a lot of dirtiness that happens in fashion that you have to deal with.

"If you’re an artist you execute by any means necessary; You don’t care how long it takes, you don't care how much it takes. When I started my brand, it was very admiral that Charizmatik operated like this, but later on as I become more seasoned, I realize why Charizmatik failed. It was too pure as an art form.

"The 'Listen to Your Heart' tee and others from the brand were always a favorite of mine, I guess because I heard it straight from Zen’s mouth and got the concept. As a design, it’s whatever. I think it was just more of a personal thing from my standpoint. Charizmatik had such an important effect on the development of Staple and although we were friends there was a bit of comradery and competition happening as well as we were trying to one-up each other with each collection. Zen would always one-up all of us.

"Even though I might have more of a balanced business mind with Staple, there’s that seed of Charizmatik that I’m always trying to inject in Staple. Just some level of thinking and the whole concept of positive social contagion that we always try to have in every piece of clothing. It's like a little bit of Zen’s spirit is in all of our clothing. It was important to have that sort of clique back then, we would travel to tradeshows back then and complain about the industry."

Era: The Wonder Years

"This is just a very clever T-shirt design. It’s not the most groundbreaking thing. They took the Milton Glaser logo and did their flip on it and added their graffiti sensibility. It’s almost like this was a poster that they could have just tagged over and made a T-shirt out of it by chance. But the slight cleverness of taking the “I” from the existing logo and adding the second syllable of their crew to it. You know it’s nice, it’s nothing Earth-shattering about it, except like, 'Oh, that was good. And only you guys could've done it.'"

Era: The Wonder Years

"It’s sad that when you Google 'Double Down tee' nothing comes up that is from his design. Double Down did a whole series of subway shirts back in, like, '98. They just did every train. This is pre-MTA licensing steez. The MTA didn’t even realize that people wanted these things and the MTA eventually shut Double Down down and stopped them from doing this.

"Trevor was the founder of Double Down and he probably had like a good five year run with these, where he was just milking it really hard. Some would consider that theft, some would consider that a crime. But really, the New York Subway System, you couldn’t have a more public open thing. It's like the melting pot of the world—the subway. He just took it and made shirts out of it and realized that there was somewhat of a following or an allegiance to your subway line almost like an allegiance to your sports team. Like, 'Yo I rep the six train!'

"And honestly, the MTA slept on it, and Trevor was hip to it and made a ton of money off of it, and more power to him. I don't think he stole anything. I think if it wasn’t for him, the MTA would never realize that there was a commodity that they could make money off of in their identity. If anything I think the MTA owes him a tip.

"He definitely did it first. And in fact, even before MTA shut him down, there were people that did it after him, but he was for sure the first person who did it. Then people started to bite Trevor and I remember he was really down on it. I remember him saying, 'Oh man, people are starting to catch on.' And I'm like, "Yeah, you know, there's only so much you can do.'  And then the MTA came and shut everyone down.

"You know what he did, he did a design that really, really murdered it. There was a Puerto Rican day parade in '98 or '99. At the height of when he was really killing it and printing money with these train shirts. For the Puerto Rican Day parade, he took a 6 train shirt and instead of the green background he did the Puerto rican flag background. On the circle with a 6 on it which is the train that you would take to Spanish Harlem.

"That year at the Puerto Rican Day parade, every single individual was wearing the shirt. He must have sold like 50,000 of those shirts or something. As a fellow business owner and friend at the time, I was like, 'Man, talk about striking while the iron's hot.' Just crazy hustle."

Era: The Wonder Years

"This shirt just shows the genius of Russ and how many different levels of thinking this dude operates on. On a political level, he took current events that were happening at the time with Castro and Che and Cuba. Then he injected his brand with the guerilla ape into it. The simplicity of just one color print, the use of the negative white space to form the ape head, it's just such good execution.

"I can’t state how when you’re an 18, 19-year-old kid trying to find your identity and you hate everything in life. It seems like everything is bad and the whole world's against you when it’s really not. You have this mentality of 'me against the world' and then you see a design like this and it connects. This is why I got so addicted to this culture because of designs like this. It's just so good."

Era: The Wonder Years

"Genius. This is genius design. Fuct is a legendary brand. This is what I call genius design. It’s original yet it is a flip on a well-known memorable image. He bastardized it by adding a dope pair of boobs in it. There’s statements about hot women being dangerous. You're fucked if you got a woman like this. You’re fucked because man is the shark and this woman is about to devour man. There are just so many levels of thought to this and that’s what I love about streetwear.

"A typical person that’s not into design or the culture, will just be like, 'Whoa dude, cool tee.' That’s level one. You can dig so many layers deep. You could talk about Eric Brunetti and the Fuct brand, you could talk about Jaws and the importance of the movie. You could talk about woman and man and how man is fucked. There’s so many levels on this.

"And then the execution of this is spot on. The illustration itself is dope, the printing is solid, the colors are great. It’s a perfect 10. Like an Olympic judge, I would put up a 10 because of just how he executed on the whole thing from A-Z is perfect." 

Era: The Wonder Years

"I hate putting my own stuff in, to be honest, but I do feel like this one really stood the test of time, which is one of the great markers of a good design; It sort of spans generations. This one definitely did that. I mean we did this in so many colors, so many times, so many variations.

"You know what I love about this is, is the nature of how this design happened. At the time I had a home/design studio/warehouse which is all one thing in the middle of Chinatown on Grand and Lafayette. And across the street from that was a gun shop. The oldest gunshop in New York City called John Jovino. It was operated by this fuckin' crazy motherfucker who constantly toted guns on his belt at all times. He supplied the NYPD with all of their guns so that's why he’s been there the longest. I walked into the shop strictly just because I thought it was really cool and then we started chatting about what I did and he was like. “Oh we need T-shirts, make us some tees.” He’s literally got his gun swinging. He's not hiding them at all, he's like a cowboy. And basically whenever that guy asked for anything, I would have to do it because I was so shook, I was so scared of him.

"I remember after we got into it and we were doing stuff with him, he didn’t understand T-shirt printing realities at all. So I’d walk in and visit and he’s like “Hey Jeff, we need extra large, four more. Can you get it to us?” He doesn’t understand that you can’t just make four extra large shirts. You have to do 144, you know? But with him, I would make sure that it happened like, Okay we're gonna do a run of 144 shirts and let’s just give this motherfucker his four.

"To be honest after I had started this deal, I was looking for a way to exit it because he was so stressful to deal with. But he’s a fuckin' ex-cop, he just kept tracking me down and getting me to do the shirts so this design kept running in and you know we sold it outside of his gun shop as well. That doesn’t happen in any other aspect of the fashion industry other than streetwear. No one's cutting deals on the side with a gun shop owner in any other industry besides streetwear."

Era: The Wonder Years

"Bathing Ape really pushed the confines of what streetwear could be. Streetwear came from skate and was always categorized as a $24, maybe $30 T-shirt that was just something for kids. Bathing Ape really re-defined what streetwear could be by selling shirts for like a $100 to fashionistas and rockstars. People who could easily afford Balmain or Gucci or whatever they wanted were lining up to buy Bathing Ape, a streetwear company. That really just opened the eyes of a whole different set of people to the whole culture.

"So you can argue that Bathing Ape heavily influenced the tastes of people like Pharrell Williams and Kanye West and then how those individuals added their flair of high fashion to streetwear and got the attention of the Anna Wintours of the world.  So you could see how Bathing Ape has such an important link in that redefinition of street culture."

Era: The Wonder Years

"I don’t own that much Supreme but this is definitely one that I covet. I love this. A classic photo of an astronaut walking on the moon, and then in the reflection of the helmet of the astronaut is the Supreme flag/logo backwards as if it were being reflected. Smart, awesome execution with everything about this. The Photoshoping of it was great. The sizing that you see there, almost like a Post-It size on a shirt is great; They didn’t make it oversized. And the statement it made, which was like, 'Yo, we're planting our flag on the moon.' It was a, 'We’re taking over the world,' type of thing.

"It was that braggadocious, street, hip-hop mentality, but executed with a very subtle graphic design and in a considered matter, which is why I love it so much. There’s a black border around it, like old film. In the framing of it where it usually has Kodak or Fuji film in the yellow lettering, it says 'Supreme' with the copyright and year, so they even changed that little detail. That's just nerd shit. Nine out of ten people w ill not care that you changed Kodak to Supreme. Me the one guy out of ten that did notice—I'm keeping this shirt for the rest of my life."

Era: The Wonder Years

"I just love W)Taps because often times streetwear references all these different things, whether it's skate or punk or hip-hop, and mixes it all together and then the creator adds his own flare into it. But what W)Taps does is they often reference military culture and the technical history of the military. But they're Otaku-nerds about it, where they just take the details and they magnify them, not necessarily adding their own flare to it.

"It’s almost like they take old military and make it better. They use better fabric, better printing. Everything is just amplified, and I always loved that in this brand. This was just their classic camo with their prints on it. The details of the red label on the sleeve and the woven label on the hang tag—they always took all the details to the next level. 

"Knowing Tet, he probably re-drew the whole camo from scratch. Me or any other streetwear designer would of just scanned the tiger stripe, and then recreated it and do a paint splatter on it or something like that. But Ted, he needed to redraw the entire tiger camo."

Era: The Streetwear Explosion

"Absurd was done by a guy named Angelo, who interned for me at multiple jobs. He was a photo editor and an aspiring photographer. And he had a T-shirt line called Absurd, which was short-lived, but made a big impact when it was available. Angelo went on to become the head of everything at Supreme. He’s like James Jebbia's right-hand man now at Supreme. A great hustler, awesome kid, and now he’s ruling the world with Supreme."

Era: The Streetwear Explosion

"Heavy, heavy shirt mixing in current events and political statements, which I think is important for streetwear to do often. It can't always be fun and games and photos of rappers or caricatures of moments in time. Sometimes street culture itself has to be the art form that sort of makes a statement that no one else can. A shirt like this is really important. And im glad they had the balls to do it."

Era: The Streetwear Explosion

"I picked this shirt not so much from a graphic standpoint but what it meant to street culture that a very urban hip-hop entity, like Dipset, who maybe just a few years prior to this might have signed a deal with Johnny Blaze clothing or whatever, now chooses to do a collaboration with Supreme.

"This raised the bar on where streetwear was going at this time. It opened it up to a whole new audience so now all of a sudden these fans of Dipset were like 'Oh shit, what’s this Supreme shit? Barbarua Kruger, what?'

"It’s funny how people who listened to Dipset all of a sudden had Barbara Kruger in their vernacular now. The importance of this shirt was bridging the gap of what was happening."

Era: The Streetwear Explosion

"Perfect logo tee. I think the lore and rumors of who and what designed this is kind of complicated. I think A-Ron from Supreme takes credit for a lot of this. There are other people who said they did it or it was their thing, but I give the credit to A-Ron and I think it has his stamp all over it.

"From his pedigree coming out of Union and Supreme, this shirt was a perfect passing of the torch of that world. Look at Union and then Supreme and then aNYthing and you can see the lineage. The execution of it was really good, flipping on the New York Giants' logo. The name of the brand—it’s a light bulb moment. I could just imagine when they thought of this brand, this name, this logo. It's genius. It's a New York thing. It's anything. Too many possibilities."

Era: The Streetwear Explosion

"I put in the 'Gun Show' tee from Rogue Status because, when this came out, it was so mind-blowing and it took that rebel mentality of street culture to that Nth degree. It was like the all-over print thing was becoming a trend in street culture and to then put something as aggressive as automatic machine guns and pistols with the all-over print. This is worse than just saying 'F-U-C-K' on a shirt. You can’t even get through customs with this shirt on, that's how aggressive it is.

"And it's awesome that somebody would do that to a shirt, and it’s awesome that the T-shirt as a medium has the power to do that. Quite honestly, this stage sort of passed kind of quickly, as it should, because it's so damn aggressive. How many kids can actually wear this? You’d be scared if you saw a mall full of kids all wearing this same shirt. It had to pass sooner or later but I think taking it to that level was important for street fashion to do."

Era: The Streetwear Explosion

"I don’t really like putting my own stuff in but I do feel like the pigeon is something that deserves a spot on the mantle of street culture. We designed the shirt back in the end of 2003, early 2004 to go along with our Nike Pigeon release. Honestly, when I made that shirt, I never thought that I would make it again. Funny, right? I thought, 'I'll just do this for this one thing, and I'll never do it again.'

"Years and years and years later, on iterations and iterations later, on cut and sew, on chino pants, on water towers, it’s crazy where this bird has taken things to. It’s a testament to how sometimes when you do something that you believe in, it doesn't have to have a reason. There’s no justifiable business plan for putting a rodent vermin on clothing. If I went to any bank or investor and I was like, 'I'm gonna put pigeons on shirts and sell them. You want to invest in me?' Everyone would say no.

"But it just shows that if you believe in something and have a reason for it, slowly but surely over time you’re going to gather a following of people that are going to believe in your story and hopefully follow along with you and go for the ride. And it's been a crazy ride from this first shirt."

Era: The Streetwear Explosion

"I remember we sold this shirt at Reedspace, I was really impressed with it because it was representative of a new trend in streetwear where things weren't predicated by your brand’s logo on the front and center of the chest. You look at streetwear now and how it’s all about floral prints and polka dots and stuff like that. This T-shirt was a fresh look at what streetwear shirts could become with patterning. Obviously most of us couldn’t get into cut and sewn yet, it was just patterning and what we could get on a tee. But it was the precursor to what was going to come which is what we see today, all the beautiful wovens and hoodies and stuff like that.

"Now the industry is big enough that we do our own cut and sew in our own patterns, but it was cool to see this in its beginning days. Back then, this shirt's print just bled off the bottom of the hem. It wasn't a clean center print, instead it was bumpy where it printed over the stitch line but there was something that was really cool about it."

Era: The Streetwear Explosion

"This really encapsulates the essence and spirit of streetwear. It still happens to this day every often where sometimes you make a design that just screams. You just want to be heard. A design like this is just making a statement that begs for argument.

"People are going to love it and people are going to hate it and The Hundreds and Bobby and Ben are really good at polarizing people and making you make a decision of whether you want to love or hate them. That’s what they're really good at and they’ll take a hater over a non-opinionated person any day. They love doing designs like this and I think it really is the spirit of streetwear when you see stuff like this."

Era: The Streetwear Explosion

"So this one, in my opinion, is just awesome graphic design. Super simple and broken down, but this is a very elevated form of graphic design. It was actually the skate industry, moreso than the hip-hop or the urban industry that pushed the graphic design element of streetwear T-shirts. Hip-hop T-shirts tended to be blingy and very ostentatious and skate tended to break it down and go more simple, and more simple, and more simple. You look at a logo like this and it’s just like a two point hairline stroke creating a logo that's pure simplicity and that’s what I love about this."

Era: Streetwear 2Day

"Any Undefeated tee could really be considered top fifty just because of the strength of this mark. Five stripes gets you the win in the playground. It’s just one of those genius things where Eddie [Cruz] just tapped on something and he deserves all the success that he gets out of this because of how strong of a brand he’s created with Undefeated. And how also adaptable this logo can be with different things. You can just put different fills in it. You know it goes with a side of shoes, it's just an awesome identity.

"You don’t need to see any words in it to know what brand this is. And he’s done it in such a short amount of time, too. On top of that it wasn’t like the Milkcrate logo or the Obey logo where it was a creation. Everyone knows what these five strike offs are, we’ve seen it all our lives. It's not anything massively unique. The only thing somewhat unique about it is the positioning and the thickness of the lines. But other than that it was all his marketing and his drive and his hustle and his persona that made this a logo, it's incredible."

Era: Streetwear 2Day

"Another one of those face-palm shirts. We sold this shirt at Reed Space and we couldn’t keep it in stock. It was one of those tees, one of those designs, that makes you say both, 'How did nobody think of this?' and 'It's just so awesome.'

"Denis [Iderman] and Ray [Mate] didn’t change a thing, except 'Hustlers' I guess, 'Hustlers' doesn’t have an 's' on it. But other than that it’s straight rip-offs of logos repositioned and placed to say something perfect without even needing any sort of modification whatsoever. It’s a very, very, very smart design. It’s a hallmark of what a good streetwear T-shirt is. This is a great example of that."

Era: Streetwear 2Day

"Diamond is so big now. It’s transformed so much. Diamond is such a ubiquitous thing with its brand now that people often forget that it has roots in shirts like this. You almost forget they used to do shirts that had curse words, and were riffs on multiple reference points of culture like Iron Maiden and the devil and graffiti and repurposing iconic imagery, and this was executed so well.

"Diamond is a brand where they realized the business of the future of street culture. Diamond is fast becoming the first $100 million true streetwear brand, it's probably going to happen next year. But to show where their roots came from is pretty dope."

Era: Streetwear 2Day

"Nom de Guerre—one of the greatest streetwear brands. Short-lived but really tried to push the envelope on streetwear and high fashion and Japanese craftsmanship. It had so many of the right elements, and unfortunately couldn’t survive the times.

"In all honesty, it probably didn’t help that Nom de Guerre was a four-headed partnership. There were four owners involved, and when you have multiple partners it's hard. PNB was the same. PNB had four partners as well, and I think it’s an impossible task to create a company where all four partners can maintain happiness. Eventually, it’s just gonna break apart as a team.

"This Arabic all-over tee was great. This tee came out at the tail-end of the all-over print phenomenon. This is such a smart shirt because it came out probably right around 9/11, where tensions were at their highest with the Middle East. To put out a shirt in Arabic at that time was so blasphemous. It's like putting a swastika on a shirt in that sort of political climate.

"Then to do it as an all-over print T-shirt, again, it was streetwear saying, 'Fuck you. We’re gonna do what we want to do, we’re not gonna do what you say. We're actually making you have a conversation about this.' This shirt probably spawned so much conversation, and that's what was dope about it."

Era: Streetwear 2Day

"This goes back to when I was talking before about Bathing Ape and how they were sort of the crossover bridge between streetwear and couture and high fashion. I just wanted to put it on this list because of the importance of it.

"If you had Nigo from Bathing Ape trying to swim upstream and take streetwear roots but try to emulate high fashion, this was the opposite. This was Comme des Garcons, who was couture and high-fashion all the way from its inception, trying to swim downstream to the streets and capture some of that street hustler mentality, which they did from a financial standpoint extremely successfully.

"So now you have all these rappers wearing Comme des Garcons and you have street dudes who wear Timberlands and baggy jeans, rocking a heart on their shirt. I wouldn’t be surprised if this Play collection from Comme des Garcons made more money than all of their other collections all time. You know they got sneakers with Converse, they got polo shirts with embroidered hearts on them, and it just never ends."

Era: Streetwear 2Day

"This is by Aurel Schmidt, who is one of my favorite artists, she’s just crazy. Her style is insane. I was a fan of her work for a while. I’m a fan of Opening Ceremony as a business model—I love what they do as a business. And then when I heard that these two came together for a series of shirts, I was both sad and happy. Sad because it wasn’t Staple that hit up Aurel. But happy that someone’s doing it and that I could go spend my money on it and support it. I love the way that they executed this. They had her illustrate every letter of Opening Ceremony. There's an 'O' shirt, there was a 'P' shirt, then an 'E' shirt, and on and on.

"This one has used, bloody band-aids. That’s her style. She just has a really demented, sick, perverse style, but her technique is so on point. She mixes these two worlds of gross dementia with beautiful execution. You love it, you love looking at it, but if you don't look deeply it’s just disgusting 'cause it’s so raw.

"The shirts that they did it on were these super fashion-y thin shirts. And it kind of goes into that category of high-fashion couture, avant garde, but executing it in a streetwear kind of mentality. So that’s why I love this. I love when that cross-over happens. I think it’s always really interesting when you see people who are outsiders to street culture do their interpretation of it."

Era: Streetwear 2Day

"I really love UNDRCRWN. I always loved what they did. This style of caricature was popular in the '80s; If you were a sports fan you know this. And then whatever incredibly talented artist they got to do hip-hop stars, hip-hop legends, and then take it a step further by doing a hip-hop legend dressed up as an athlete was just hilarious and the execution was spot-on.

"If you compare them, UNDRCRWN could be the more commercialized version of No Mas. It also had the street culture, jock-type fan, but it was a little more fun. I think that opened up their distribution wider than No Mas, which tends to be very heady and tongue-in-cheek. This one’s graphically very funny and a lot more people can get into it."

Era: Streetwear 2Day

"You’ve got the biggest sports brand in the world in Nike. You've got one of the most talented, creative, high-end fashion designers in Jun Takahashi of Undercover. They came together for Gyakusou, which is a great thing, but it has nothing to do with streetwear. This T-shirt that they made, 'Running Monks,' is so cool to me because it’s sports and it's high fashion but the execution of this T-shirt to me is very streetwear. It’s a T-shirt that has a big statement on it which is kind of like a streetwear thing. And then 'Running Monks' is very much an inside joke. It doesn’t mean anything to anyone unless you’re into what Jun does with running and what Gyakusou is so it’s talking to a very niched subset.

"I just love that a $20 billion company decided to just do a shirt as an inside joke for some people that were really into the culture. It just goes to show where street culture had gone. I think if it wasn’t for streetwear’s place in fashion, Nike would not even think to do something like this, so it kind of shows the impact that we have created."

Era: Streetwear 2Day

"Awesome design by the Rocksmith boys. As a competitive designer, sometimes you see at a design like you sort of face-palm your forehead and you’re like, 'Ah, that’s good. Fuck! Why didn’t I think of that? That's really good.'

"You got Basquiat, the king of art. Biggie, the king of hip-hop. Put it together, no-brainer but at the same time most dudes have been around for like five decades combined and no one thought to do it. And then they did it and it was like, 'Of course, now you get to have those million dollars from the sales of this shirt.' I put this in strictly because of that feeling of like 'Shit, why didn’t I think of that one?'"

Era: Streetwear 2Day

"I’ve always been a really big fan of No Mas and I don’t understand why they’re not more successful than they are. They’re so unique, there’s really no other streetwear company that just makes funny references to weird moments in sports. Maybe that’s the reason why. Maybe it's because to be in their audience, you have to be a super, uber nerd. You have to be that guy that watches Sportscenter on loop four times in a row everyday.

"Usually those guys aren’t fashionable guys. That guy doesn’t go to Reedspace and Union, so maybe that's why. The number of those armchair quarterbacks that play fantasy football and watch Sportscenter and also go to Union are very few and far between. But that's really who their customer base is. I’ve always been a big fan and this design just poking fun at Darryl Strawberry and his ongoing cocaine and crack problem and putting his face on a 'Say No to Drugs' shirt is the equivalent of an emcee shit-talking to another emcee. This is great."

Era: Streetwear 2Day

"I wanted to put in the World Tour tees, where Stussy had different artists writing their important cities in their hand style. This was for the 25th anniversary of Stussy, an incredibly smart campaign that can be repeated over and over again. You just write the template and you go out and you're like, 'Alright, everyone that we know in our Rolodex should do this for us.' It's pretty easy to roll it out and it’s pretty easy to execute. But it doesn’t look half-assed, every single one is a unique art piece unto itself.  And you just wanted to get all of them.

"It also taps into all the different cities, which is genius. For example, with this particular shirt, if you’re from Compton you might never want a Stussy shirt in your life but now you need this shirt because it says Compton on it."

Era: Streetwear 2Day

"A design that represents so much of where street culture is today, and how it's been accepted by pop culture. In this case, even the designer label they're making a parody of accepted this. The explosion of this design is incredible. I would love to see an infographic on how much this one design made SSUR compared to all other T-shirts he's designed combined."

Era: Streetwear 2Day

"So this is one of those shirts that's like an inside joke shirt. It all started from Milton Glaser who’s a legendary graphic designer. He did the 'I Love New York' logo and then people started to flip off of that. Other cities flipped on that logo, too. I love SF shirts, I run New York, blah blah blah. So this was just like the nail in the coffin for all of those shirts. Go fucking love your own city and get the hell out of New York. It's a very New York sentiment, kind of like a New Yorker attitude and this shirt, this design, exuded this attutide.

"It’s hard for a shirt to do that, it’s not easy for a shirt to have its own swag to it but this shirt did that. The execution and the design is good too. I always like this one for some reason. The other thing that was good and clever from Reason’s standpoint was that it doesn’t say get out of New York. It was go love your own city. So even though it had a New York mentality, if you bought this and wore it in Chicago, it would make sense, too."

Era: Streetwear 2Day

"From a design standpoint, this shirt is, aesthetically-speaking, not 100% my cup of tea. But it couldn’t better visualize all the inspirations that went into streetwear. Right in your face, you got sneaker culture, sport culture, hip-hop culture. You got the art and illustration from Tribe. You got 'Keep Bouncin',' which is the quote from Tribe Called Quest. You got Micheal Jordan in the slam dunk contest, so you got the sport element. You got him rocking IIIs, which is the sneaker concept. It’s an all-over print, which is indicative of the street culture that was happening at this time in terms of the trend. Every inspirational trend that was happening in street culture put into a blender and came out on a shirt and this is that shirt. Whether you love it or not is one thing, but it says it all. 

"This shirt could have been sued by four or five different entities. Tribe could have sued them, their record label could've sued them, MJ could've sued them, Nike could've sued them, Brand Jordan could've sued them. ESPN could've sued them, I think Gatorade could've sued them, the NBA could've sued them. They should have gotten eight cease and desist from this T-shirt.

"I always said to myself if I don’t get one cease and desist a year for Staple, I’m not doing something right. I wanted to get sued every year and I was doing well for a whole stretch when I just kept getting sued. But Staple is now at a point where it’s too dangerous to get sued now. But back in the day it was cool to get a cease and desist every year.

"It meant you were not giving a fuck and it showed moreso that you were getting the attention of the people you were trying to bother. I remember I did a Hummer shirt, a play on Hummer, and got a cease and desist from GM the parent company for Hummer. I was like, 'That’s so crazy! Some motherfucker from General Motor was looking at a staple shirt.' I was so happy about that."

Era: Streetwear 2Day

"You know when an art movement is so advanced, it gets to a point where it reflects on itself. It's sort of like neo-classicism. And I think this is a good example of that here. Supreme x Hanes is a very interesting collaboration because Hanes is essentially an undershirt company. To the casual user you might think that this is not a designed shirt. This is bullshit—someone put a fucking tiny little logo in the corner and called it in.

"But I can tell that in actuality what probably happened was that the designer of the shirt looked at the history of streetwear, and had seen where it’s gone from the '80s, '90s and 2000s. When this shirt came out in the late 2000s, it sort of made a statement like, 'We’re not going to do what you would expect us to do. We’re going to do the unexpected but also respect the collaborator that they're working with, which is an undershirt company.' That's the genius of the shirt.

"It's an undershirt. You wear it under your sweatshirt or hoodie, and maybe the undershirt is untucked and it peeks out from under the waistband. That’s all you see, is that little hint. In that way it’s genius. Like I said, to the casual guy it's lazy but it's definitely not. That's the genius behind great design. It's made to look totally simple. But there’s a lot of thought and weight that goes behind something like this."