Neil Chester In Transit

Neil Chester doesn’t do categories. Skater turned filmer turned creative director (and self-proclaimed ‘cycling degenerate’), he’s been chasing motion in all its forms since the VHS era sparked a generation of DIY skate videos. Whether behind the lens or rolling through the city—these days more often on two wheels than four—his eye is rooted in subculture, where speed meets stillness and every frame captures a story.

Now based in Amsterdam, Neil’s journey has carried him from local skate spots to shooting the recent MAAP x Pop Trading Company collaboration on home soil. With an insider’s feel for the city and a foot planted in both skate and bike scenes, getting a perspective through Neil’s lens was the only choice. And his throughline’s always been clear: create with intent, chase the feeling, and never stay still for too long. We sat down to talk creativity, cameras of choice, fellow Aussie Nick Cave, and what it means to clip in and get out there…

I actually don’t really consider myself a ‘photographer’ in terms of it’s not my job one hundred per cent, and I feel it would be kinda unjust to people out there doing it full-time. I work as a creative director at an agency, but my background is in skateboarding. I was a skate filmer for many years, so the moving image was my first real creative passion—from movies and watching a ton of music videos, back in the 90s when they were such an awesome creative force.

It was a natural evolution to film your friends skating—you just organically wanted to make a video, so I got into that and it grew from there. And I’m from the era when skate videos blew up and took it worldwide out of California.

I’ve always said that the evolution of skating kinda follows consumer video cameras being easily available—from the early Powell and Santa Cruz videos shot on film in the late 80s to H-Street and New Deal videos just being homie videocams. Suddenly you can try a trick in the street for hours on end, so it progressed fast. Video changed skating from tricks to music, clothes, and attitude. It fueled the culture, which is what it’s lacking now in the day of short-form social media dominance.

I’ve always had both still and video cameras. Back when I was filming a lot of skating, you needed to capture the full trick — including the rollout — so your framing had to move with the action. But over time, I started preferring to stay still and capture a single moment instead. That’s why I mainly shoot photos now.

For me, photography has become a kind of hybrid — part creative outlet, part occasional paid work, and part hobby or whatever, kinda like cycling. I can’t draw or play an instrument, so I shoot photos.

Nothing too specific, just years of seeing great cinematography and photography inspires you. Part what I was immersed in on the street, and part what I choose to immerse myself in by digging more into the techniques behind it. I’ve always been a bit of a dreamer too, which I think helps to maybe see things differently. I still see stuff today, get an idea and think, right I want to make a film or become a (proper) photographer, haha.

You just slowly learn, especially what not to shoot. Experience is key, figuring out composition or framing without looking in the lens, which I do a bunch in the street. Or how to get a particular shot, but I just shoot what is around me really, somehow try and make that look good, different or just interesting.

Just go out and do it, trial and error. Sounds old school but this process will also eek out whether you really want to do it or not. If you don’t it will soon drop off. I think you could apply this to creative stuff like photography, painting etc, or even cycling or skating; if you want to do it well, it takes time and it’s not so easy.

I shot my first photo of 2025 in late March! Although, I blame the grim Dutch winter for this. But any creative block is just mental, so it’s either working through that, however one does, or simply knowing that it is just a mental block and it will pass.

Kinda is what it is, pretty wild and it's easy to knock it for negative reasons, how it can kill sub-cultures and really affect society. But I guess it also has its positives, of which everyone has probably benefited in some small way. I try to keep a balance. The internet is such modern history, it’s kinda just starting too, crazy where it’s going to go.

Amsterdam—been here over ten years now, crazy. I came for work and just stayed. I lived in a few places, but you gotta drop anchor at some point and as you get older, it gets easier to stay put. The Netherlands is a good place, for the most part socially forward thinking, rest of Europe on your doorstep, and the best cycling infrastructure in the world, but I do need a warmer climate so we’ll see.

I’d like to go to many places I’ve not been before, somewhere that is quite remote, rural Brasil, or deep Northern Territory in Aus. Try to find a story or a perspective to shoot that from, I guess to create something that is visually appealing and has a unique narrative, which is kinda the holy grail in photography.

I’ve just known those guys for the whole time I've been in Amsterdam, which coincides with them just turning ten years old. I used to work for Converse, and Peter, one of the original POP founders, did skate marketing for the Benelux region, so I got to know him there. But in skating you just naturally mix to other skate networks and have that instant connect. Then just a natural path to working together, or I see it more as just helping each other out and they've got something good going on in Amsterdam, so it's cool to be a small part of that.

Certain artists have played a big influential role on me, Nick Cave and Helmut Newton to name a few, although they practice different genres, to me at least, they both communicate something really special beyond the image or song they create. Nick Cave is simply the world's foremost writer of love and emotion, and Helmet is a master at using the scene to tell a story - fashion photography started and ended with him.

Kinda just gave that away! Nick Cave and the Bad Seeds has been a soundtrack to more than half of my life now. They’ve certainly helped me to grow up and learn human feelings - love, lust, loss, desire, hope. Also how they’ve evolved as a collective, that's the work of great artists, evolution. As for a playlist, geez, it would be an odd mix for sure, from 90s camp pop to Nina Simone, Springsteen, Madrugada, INXS, Mayorkun, so many.

Oh man, I’ve been into cycling almost as long as skating, I think I first watched The Tour in 1989. Seeing all that iconography and French scenery was so good combined with the drama of a Grand Tour.

I always had a bike as a kid, but I got my first proper road bike in 1994, I think. An alu-lugged carbon Cadex 980 with Campag Delta brakes, that I wish I still had! I cycled on and off for a while and then got another ‘good’ road bike around 2005 when I was living in London. It’s kinda ramped up to now, where it’s all I do and kinda totally replacing skating. I watch literally every race, Youtube channels and I’m a total cycling degenerate, haha.

Ok, so my take is that they are kinda the same on many levels. When you were a kid, your first sense of real freedom was when you got a bike and you could suddenly go anywhere, off your street and around the block, maybe the next town. When you get into skating, it’s similar in terms of the city becoming your playground, it's an exploration to find skate spots and visit other cities. Once you’ve had a life of skating and you get older, getting on a bike again and cycling is both mentally connecting to that first sense of freedom as a child, and how the local area suddenly opens up again like it did in skating - a ‘where to go cycling’ perspective. 

Then throw in all the gear, in skating you want a dope board, skate shoes, pants etc—cycling has that in abundance, dope bike and kit. And finally all the quirky rules, like in skating you can’t mall grab your board, or push mongo, it’s not cool. Geez, cycling has a million ‘not cool’ things about it, helmet straps under sunglasses, sock length, bib length etc. And, the two ‘sports’ are really hard to understand from a professional standpoint. In skating the guy who wins the contest, is often not the ‘best’ or most revered, and most people do not have a clue what is happening throughout a 200km bike race! 


I’ve seen my philosophy, if you want to call it that, happen to a bunch of skaters who start cycling. And most have initial opposition to wearing cycling shorts and shaving their legs! They cave in pretty soon, haha.

My road bike right now is a peak rim-brake 2019 Giant TCR Advanced SL, full Dura-Ace. Shout out to Ryan at Giant Wollongong, I got it from him very randomly in early ‘24, but it had done about 250 km, so it was virtually new. I also have a steel gravel bike, a Fairlight Secan. That thing is so good and versatile, you could cycle around the world on it...

Not sure about my dream bike, but I have said to myself that I’m getting my mid-life crisis bike this year. Full pro-rig, aero as. Try to cling onto some speed and watts in my older age. Trying to rationalise it, I tell myself I want a disc road bike for braking when in the mountains. Rim brake is fine in the Netherlands, it’s so flat.   

Whilst I like to carry a little Ricoh GR II around with me a bunch of the time, I just as much like to carry absolutely nothing. Maybe years of carrying a camera bag on my back, but I love the fact we have no wallet or cash anymore, just a phone. Even when I travel now I try to take the least amount of stuff. I was in the US for three weeks lately and I did it with just hand-luggage. That's my advice from the earlier question, get a Ricoh GR and shoot what's around you. The best camera is the one you have on you, an old term but so true.   

On the daily I can tend to do the same loop over and over, which is more a ride of  convenience when I have a free time window. We have some decent gravel out past Hilversum, so this is a good road/gravel loop and has a few things to look at other than just flat fields and dykes, which in the Netherlands can get very repetitive. I also love to actually go somewhere, not a local loop. I was down in Limburg recently and cycled home from Maastricht, rides like this are always cool for discovering new roads.

The legs of Tadej! And his salary.  


Captured in Amsterdam by Isolde Woudstra, Neil Chester wears our latest on and off-bike collections, available now.