Streetwear’s “golden age” is debatable; its evolution is more of a gradual climb with multiple summits. Yet, there is a spirit, an ethos, commonly associated with streetwear: a rebellious counter-narrative to mainstream fashion.

It embodied counter-culture, an amalgam of diverse subcultures such as skateboarding, fashion, music, etc. Diamond Supply Co., founded by Nicky Diamonds in 1998, offers a compelling starting point for understanding this evolution. Diamond Supply has experienced the ebb and flow of a streetwear brand and witnessed the evolution of a culture, one in which the brand played a consequential role.

As he reveals in the upcoming interview, his success, like that of his contemporaries, was unexpected. There was no playbook, no precedent. From different points and places, they cleared, carved, and created their own path, driven by strong interest, instinct, and intuition.

A confluence of factors, including the rise of the internet and the digital revolution propelled them forward. None of which they could have predicted and influenced.

Thus, perhaps it was fate, or simply following his instincts, that made him an accidental architect of today’s ubiquitous collaborative culture, shaping the landscape of street culture where fashion, skateboarding, music, and countless other subcultures converge.

For nearly 30 years, Diamond Supply Co. has witnessed streetwear’s ebb and flow. While famed for the Diamond Dunk, arguably the greatest Nike SB of all time, the brand continues to inspire, designing the blueprint for its de facto successors.

“Diamond is 27 years old, and the Diamond Dunk is actually 20 years old. 20 years old this year. It’s the 20th anniversary of the first Diamond Dunk. I feel that it’s a blessing that, you know, it’s coveted… And it’s amazing Complex voted it the number-one Nike SB of all time.”

When people think of Diamond Supply Co., there’s a certain color that they associate with. How did the Diamond Blue turquoise become Diamond Supply’s signature color?

Well, in 2005, I had the opportunity to do my first Nike collaboration, and I already made a t-shirt that had the colorway of the Diamond logo in the Diamond Blue colorway with Supply Co. underneath, and it looked like, you know, it’s the same colorway as Tiffany & Co.

But no sneakers were on the market in that color, so I was like, I just laid it out on the computer. Well, long story short, I presented it to Nike, and they loved the colorway. So they made the shoe as my first collaboration, and it was called the Diamond Dunk.

Diamond Supply Co. x Nike Dunk Low Pro SB “Tiffany”

But everyone just started calling it the Tiffany Dunk because of the color, even though it wasn’t planned for that. Since then, because it was such a popular shoe, people kind of just associated the color with my brand, which is a streetwear brand, a skate brand. And, you know, Tiffany was a luxury jewelry company. It’s kind of hard to get away from it at this point because of the iconic shoe that it became.

But the original colorway that I, which I still do with the brand—most of my stuff is black and red, but people always want me to, like, when they do a collaboration or anything with me, they’re like, “Can we do the Diamond Blue colorway?” So I still run it, but just not as much.

Everybody loves the hallmark.

Yeah, people love the color. It looks good on clothes, it looks good on shoes, it looks good on everything. So I run it, but it’s definitely not my official brand color, but people like it.

Like it’s the one the culture that imposed on you.

Yeah, the culture demands that color from me. So I still do stuff, just not as much as I used to in that color.

The Diamond Dunk is a grail, so considering it came out in the earlier years of the brand’s long history, how did it feel to you to have created one of the most coveted shoes of all time?

It was really insane because I grew up a full sneakerhead, collecting Jordans and all kinds of shoes. Ever since I was young, I’ve always been into sneakers and clothes. So, yeah, having a collaboration with Nike, I couldn’t believe it, honestly. It was mind-blowing, of course.

And my brand at that time was already seven years in, because I started in ’98 and had the collaboration in 2005. But yeah, I never thought something like that would happen, that I’d have my own Nike.

And Diamond Supply is still here, almost 30 years.

Yeah, Diamond is 27 years old, and the Diamond Dunk is actually 20 years old. 20 years old this year. It’s the 20th anniversary of the first Diamond Dunk. I feel that it’s a blessing that, you know, it’s coveted, like you said. And it’s amazing Complex voted it the number-one Nike SB of all time. So that’s crazy.

Nicky Diamonds’s most famous brainchild on the cover

It was also on the cover of Sneaker Freaker’s latest book.

Yeah, it was on the covers of magazines, all this stuff. Still to this day, 20 years later, holding this sneaker grail, as you said, it’s amazing. I can’t believe, like, 20 years later, it’s still a thing.

Yeah, that’s your legacy right there. With Diamond Supply being around for 27 years now, how do you think the brand’s audience has changed over the years? Like, people who started in the beginning have grown up as well, and I’m sure there are now new people supporting you.

Yeah, so that’s really cool, too, because I meet people all the time, and they’ll say, “Hey, I grew up with Diamond my entire life, and my dad used to wear and collect Diamond.” Like, people say that.

I’m like, “Oh, I guess that makes sense.” Because, you know, 27 years of having a brand, you know, that means that when they got into it, they’re probably like 10 to 15, even 20. So, some of these guys might even be 45 or 50 years old that are old Diamond fans that grew up.

I mean, you could be a kid, you’d be 27 years old and have Diamond in your entire life until then. So, it’s a trip. It’s crazy to still be here doing what I love all this time later.

Having done this for a long time, I’m sure the brand has gone through a lot of evolutions. But what has that journey taught you about yourself and the world?

A lot of learning. When I started, I didn’t really know anything. I was just a skateboarder. So, I was just a skateboarder who was into fashion, sneakers, and design. I didn’t ever think that I was going to start any kind of brand or do anything like this. Really, it was just (about) skateboarding.

I was a sponsored skater and doing all that stuff, and I was sponsored by all these companies, and I would kind of just, like, design stuff for companies, and they liked the designs, and they’d make them, and they would do well. So, I was like, “Oh, I’m just gonna make a hardware skate team to put all my friends on the team.”

And I made skateboard bolts, then I started making t-shirts just to go along with the bolts and then those started doing well. So then, I just started designing more t-shirts, and I started designing clothes. The next thing you know, I’ve just been designing for almost 30 years now.

I’m just on a fluke. Like, I wasn’t really a designer, I guess. I would draw and shit, but I wasn’t thinking that my career and life after skateboarding would be designing. But that’s what I did. I guess I’m a designer.

Yeah, you are, for sure.

I didn’t even plan on that.

One of the special collaborations Nicky Diamonds did for Culture Cartel 2025

And it’s at a time when you were at the vanguard. There was nobody to look up to or to set the standard. There was no precedent back then.

There wasn’t, yeah. I wasn’t, like, looking up to anybody. I didn’t have influences or anything. I was kind of just doing it. It kind of just happened, and as I got older and started paying attention to other things going on, I started learning more about other brands and things like that that were outside of just skating.

I was just skate-focused my whole life. That’s all I cared about. Then I started getting into more design, and obviously, sneakers and stuff, but I didn’t really know about other small streetwear brands. So over the years, I made a lot of friendships with young streetwear brands, even though I was from skating.

I started doing lots of collaborations. That’s really what helped propel Diamond from being just a skate brand. And, of course, doing the Nike collaboration, but also doing collaborations with all these streetwear brands. It really took Diamond from being skate and being more recognized outside of skating in the rest of the world. Yeah, just partnering with people.

Like Bobby Hundreds and The Hundreds.

Yeah, back then, it was The Hundreds, Crooks & Castles, 10.Deep. A bunch of brands, but I also started doing a lot of collaborations with young rappers. Back then, I collaborated with Rick Ross, Big Sean, Wiz Khalifa, Curren$y, Cassie Ventura, P. Diddy, and The Lox. Just tons of people, and back then, people weren’t really doing that.

So I kind of set that off, the whole “brand x rapper”. Like, I was kind of the first one to really be doing that, so that helped me as well with the brand being recognized all over, outside of skate, and now outside of streetwear, into music. So now I kind of, like, built the whole culture around the brand. Kind of by mistake, but it just happened that way.

A Diamond Supply Co. x PUMA Clyde waiting to be autographed

So it isn’t just the Diamond Dunks that is your legacy. It’s creating, whether unintentionally or by extension, the culture of collaborations with different entities, brands, and music.

I, uh, unintentionally brought music, skateboarding, streetwear, and sneakers all into one thing, which was, like, Diamond Life. And I’m like, “Okay, now the brand’s Diamond Life and all my fans are Diamond Lifers.” And that’s how I kind of built the brand. But, yeah, it was a trip.

Now, all of a sudden, I have outside cultures of street fashion and everything surrounding the brand. That’s how the brand blew up the way it did back then because all these things influenced it because I was into it. Unintentionally, it’s just kind of how I did it.

And the internet was just starting to boom with blogs and stuff. Back then, I was on Hypebeast forums and Sole Collector, posting pictures of all my apparel. I kind of, like, set that off, and people weren’t doing that. They’re like, “What are you doing?” And I’d be like, “I’m promoting the brand.” Like, I’m posting, and people thought I was weird. They’re like, “Why are you talking to all these people on the internet?” Because people didn’t understand. It was so long ago. It was, like, when all this stuff was new.

Pretty much whatever is being practiced here (at Culture Cartel), all started with you.

I wouldn’t say it all started from Diamond, but I did have, I guess, something to do with a lot of it—unintentionally.

A special partnership with Performance Motors

Being at such a unique time in history, when everything was just starting to grow, I’m sure there are so many lessons. Like, the life you’ve lived is so unique. Yeah. Do you have plans to, like, write a book about it? Similar to like Bobby Hundred’s This Is Not A T-Shirt?

No, people always ask me that, about doing a book. We did do a little book that was with Frank 151. We did a book back maybe ten years ago. But it wasn’t really a book of me telling my story. The way they did it is they interviewed a bunch of people like my peers. They interviewed, like, a bunch of rappers. They interviewed a bunch of clothing designers. They interviewed a bunch of skaters about me, which was interesting. So they asked people questions about Diamond and what Diamond meant to them.

So there’s all these interviews with people talking about what they think of Diamond. So that was kind of cool, but you should check it out sometime. It’s an interesting book.

It’s over ten years ago, but it’s kind of cool getting—I mean, when I read it, it was so interesting seeing people’s perspectives on what they thought the brand was and what it meant to them. There are some pretty cool people in there.

I just saw it again, like, recently. I didn’t see it for many, many years, and then I just skimmed through it. I found it in my storage, and I was like, “Oh, what a trip. Crazy book.” But I haven’t thought about doing my own, like, the story of Diamond, or archives, or anything like that. I don’t know. It seems like a lot of work.

The Diamond Supply Co. issue of Frank151

The way and the fact that your story is being told by other people just alludes to how meaningful the brand has become to them.

How did you pivot from, like, just apparel to designing your own footwear, clogs and, like, mules?

From designing skate products to designing clothing to designing footwear, to—I even made my own Diamond shoes in the past. I just design all kinds of stuff. We’re actually dropping radios here today that I did a collaboration on. I just like designing and making things, so it doesn’t matter. I feel like I can just make whatever I think is cool.

I’ll just design something, so it’s not like I’m just doing footwear or apparel. I’ve made furniture, I’ve made all kinds of things. I’ve designed the houses that I’ve bought, torn them down, and had them built. Like, I’m just into making shit, and again, I never thought that that would be my path of being a skater, but it just evolved into designing all kinds of stuff. It’s fun. That’s what I like. It’s my passion, just making things.

The Nicky Diamonds-designed Bumpboxx

But having done this for decades, how do you still stay creatively inspired?

I don’t know. I just like making new things, but I don’t look for anything for real inspiration. I just came up with ideas. Obviously, I’m inspired by everything around me, everyone.

Growing up being around so much stuff, being part of streetwear, being a part of music, growing up listening to all kinds of music as a kid, from punk rock when I was a little kid skater to hip-hop to reggae to rock to heavy metal. I was always into all kinds of different things: art, architecture, and everything.

So I guess I’m inspired by everything I’ve grown up around, even sneakers and clothes. I guess I just draw inspiration from things that are in my mind from my past when I’m designing because I design all my stuff. I don’t have a design team. I’m the only designer for Diamond. Yeah, I design everything that you see. From all the graphics and apparel, I do it all. So I guess I just kind of draw inspiration from my past and things that I’m into at the time. So it’s always evolving and changing.

My designs kind of have a [cohesive] aesthetic. If you look back at old Diamond, you can kind of tell my new designs because it’s coming from me. I don’t try to make things look the same, but I’m always like, “This looks like I can look back on stuff and be like from 15 years ago and be like, ‘Oh, this looks like something I would still drop today'”. But then sometimes I do things off the beaten path and do kind of random stuff that I might be into.

Trends and fashion change, and how I dress changes sometimes, and I go back and forth. I saw a picture of me a couple of weeks ago that was from 20 years ago, and I was like, “I dress like that right now.”

I used to wear baggy pants, Jordans, and oversized tees. Trends change, and I’m probably influenced by what others wear, too. It’s like, you see everyone wearing baggy pants again, and it seems normal to return to them. It’s funny how that works. I’m like, “Oh, I used to dress like I used to back then again.” So it’s just how it works.

“I don’t have a design team. I’m the only designer for Diamond. Yeah, I design everything that you see. From all the graphics and apparel, I do it all. So I guess I just kind of draw inspiration from my past and things that I’m into at the time. So it’s always evolving and changing.”

You are kind of just influenced by everything around you. So that’s how trends and certain things, I feel, become really popular. Obviously, people wear their shit, and they style things their way, and you have their fashion sense. But for the most part, I think there’s an influence from everyone around you that dictates what’s trending, even like foam slides.

Back in the day, I would have never thought Crocs were cool, you know, but then once you start seeing everyone wearing them and they’re doing all these different collaborations, then you’re like, “Oh, those are pretty cool.”

Like baggy pants and oversized T-shirts, five years ago, we were wearing something different than we’re wearing today. It’s all kind of an evolving thing from the ’80s, ’90s, 2000s, 2010s. People were wearing bell bottoms in the ’70s, and then they got tight, then in the ’90s, we’re wearing super oversized pants, and now people are doing it all over again.

So, I don’t know the trip, but it is always evolving. I’m always changing how I dress, kind of, but I design the same way. It’s always evolving.

The Coupes De Diamant Slides as worn by Nicky Diamonds himself

For the slides and the clogs, there’s a vibrant color palette for all of them. Is there a reason behind the choice of each color?

I actually have a lot of slides coming out. I’m trying to get it on the calendar to drop one, up to three or four slides every month for the year. I have like this whole plan of all these different colors because I love them so much. I wear them all the time. I’m even wearing the clogs.

Even on this trip to Singapore, I usually pack all my sneakers, but for this trip, I just packed these (the clogs). I decided to just wear these every day because they’re so comfortable. I still wear my other shoes, but I think I wear these clogs more now. Not only because they’re my design but because they’re just super comfortable. Nowadays I’d rather just wear something I could walk around in all day like I’m walking on pillows.

And they’re good for every occasion now.

Yeah, and they look crazy. So everywhere I go, people ask, “What are your shoes?” They’re always grabbing attention, which is funny, even like old people and stuff. Someone always has something to say about it because they look wild.

The Coupes De Diamant Slides in red

And there’s no better marketing than wearing it yourself, right? Lastly, is there any advice you would give to the younger Nicky Diamonds starting?

I’ve gone through so much in my career of doing all this, so I can’t say what to do and what not to do because I feel like everyone’s on a different path, and things happen differently for different people. And I feel like things are meant to be. I feel like when I started the brand and the way that things went, it just happened the way that it was supposed to. And I feel like that with anyone in any career, anything that they do in life. I feel like their path is kind of already set for them, and they’re just living.

So I wouldn’t even know what to tell somebody. I feel like follow your heart and passion and just do what makes you happy.

“Everyone’s on a different path, and things happen differently for different people. And I feel like things are meant to be… And I feel like that with anyone in any career, anything that they do in life, I feel like their path is kind of already set for them, and they’re just living.”

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Source: SNKRDUNK; Nike; Taschen; Frank151; Culture Cartel

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