The Shirt List interviews Nathan W. Pyle

Even before I noticed his designs I noticed his name, just because it was so unusual to see someone’s username as an email address. Yes, Nathan W. Pyle goes by the name nathanwpyle at and yes, I have asked him about it and yes, he gave a satisfactory answer. Now you know what it’s all about, or you will if you read even just the beginning of this interview.

Of course it is not just his name that caught my attention. He has a knack for making very simple but very clever and funny designs. You don’t have to think about them either, you just look at them and understand. See the Batman/chess design above for a typical example. (Will be available on Shirt.Woot! soon.)

By day he works as a creative in TV production and at night he dons a cape and prowls around the dark streets of Gotham fighting crime in the evenings takes the New York public transport home while giving his best design ideas to the people sitting next to him. (He has ideas to spare.) He is also a sports fanatic and I really don’t know how he found the time to give this interview but he did and we appreciate it.


I’m guessing that your last name is not really so the logical first question is: what does the W in Nathan W. Pyle stand for?
William, first name of my Grandfather on my Father’s side!

You are the only person I have heard of using their email address as their username. What made you decide to do this?
When I first chose my user name for Threadless, I was surprised the box allowed me to keep typing after 10-15 characters, so I just kept typing and typing to be silly .. but then realized this would also make me easy to contact. And so it was.

I do enjoy spam when it’s ALL CAPS and from someone royal.

Do you get exorbitant amounts of spam and if so, do you read it all?
I do enjoy spam when it’s ALL CAPS and from someone royal. But fortunately for me I don’t get much spam, and I don’t think most spam-bots trawl Threadless looking for user names that are emails. (You said I was the only one after all)

See Arm for Details T-ShirtCleanup on Aisle Two T-ShirtItalyc T-Shirt

*Cleanup on Aisle Two (center t-shirt) is a collab with Mitch Ansara aka spacesick.

I read somewhere that you work in TV production. Can you describe a typical work day for us?
Sure! I produce news-magazine and documentary style shows in the non-fiction TV world. I’ll ballpark these numbers, but I spend 34.4 percent of the time writing scripts at my computer and then 29.2 percent sitting with an editor helping put a show together and then 24.7 percent out on shoots, interviewing people, etc. and then meetings, scheduling, refilling my water bottle, etc fills up the other 11.7 percent.

I believe you live in New York. Is that where you were born and raised?
I was born and raised in the beautiful Buckeye State! O-H-I-O forever. I love New York though, and I have always wanted to live here. But I enjoy visiting family and driving my car to Chick-fil-a back in Ohio.

Apart from working in TV and designing awesome tees what keeps you up at night and busy on the weekends?
I love taking photos of New York and exploring the city. I am amazed that there are streets less than two miles from my apartment that I have yet to walk down. And I meet new, amazing and talented people every day.


You have a full time job but it looks like you have submitted over 150 designs to Threadless. What percentage of your time to you devote to t-shirt design? 
Wow, no one ever noticed that! It’s true, I’ve submitted a lot of them. I’d say I spend a solid 30% of my week designing. I’ve taken a liking to doing more collaborations with professional artists because I have so little extra time some weeks, and I have more ideas than I have time.

Why t-shirt designs and why Threadless?
1) It feeds my constant need to create 2) T-shirt art is so practical and personal, and I love connecting with people who enjoy laughing at the same things I do – all over the world! Which is exactly why THREADLESS – their reach is ever expanding, and I’ve made friends from dozens of countries through them. It’s really an amazing community and collection of extremely talented, smart, funny people.

If you couldn’t create art what would you do in your free time?
What kind of crazy hypothetical world are you creating? I’d probably play more sports because I love doing that about as much as anything. SPORTS.

A short story about X designLuke designScreen with envy design

Many artists struggle to find a theme but that is clearly not an issue for you. Do you see ideas for t-shirt designs in absolutely everything?
Yes, and I credit my city. New York makes it easy to notice hilarious visual jokes all around you, everywhere. And I have forgotten so many great ideas too because I got distracted by something new – it’s why I have to text myself constantly or write things in my notebook or tell the stranger next to me on the subway.

Could you describe your typical design process from concept to completion?
I’ll often post sketches on the internets and then allow the wonderful community of artists and thinkers at Threadless help me weed out my really really dumb ideas by saying really polite things like, “You can do better, Nathan” or “No, not that one.” Then I’ll take my laptop to one of the city’s 100 Starbucks locations and drink iced coffee and watch Netflix instant while I design and then I’ll trudge home and buy a half-gallon of milk for 3.40 at the bodega across the street. $3.40!


You’ve had a few tees printed at Threadless but the big news now is that your Poison T-Shirt is the first Shirt.Woot tee to sell more than 4,000 shirts on its first day. Was this a surprise to you or did you know that this design was special?
Ha! If I had been more prompt in returning your questions, this would have been more relevant to right now. Apologies! But POISON was a heartfelt tribute to one of my favorite movies of all time, The Princess Bride. It received a decent smattering of applause when originally posted on threadless but I knew someone somewhere (and thousands of someones it seems) would really like it. Surprised it sold over 7,000? Not really! It was totally conceivable. So I’m so thankful the folks down there at WOOT! picked it up. It’s one of my favorite designs!

Princess Bride Poison T-Shirt at Shirt.Woot!
This Princess Bride themed shirt by Nathan broke records at Shirt.Woot! (No longer for sale, sorry guys.)

Do you remember your first t-shirt contest win? If so, what was it and how did you feel?
My first win was on Threadless! I had never heard of this kind of design contest thing until 2008. It felt incredible! More on that later!

108 Objects from Flight 815 by Nathan Pyle at Threadless
Nathan’s first ever print was this LOST themed goodness at Threadless.

Which of your t-shirts is your favorite?
108 Objects from Flight 815” was my first print on Threadless and shall forever be my favorite for that reason. At that point, I had already submitted over 100 designs to Threadless, and getting that first ‘notification’ email was just an unforgettable feeling of gratefulness. I am not a patient person in most cases, so the fact I’d persisted that long was a big deal for me. Threadless famously sends artists an email that says “Congrats, Your design was selected” and when I read those words it was like the clouds opened up and light shone upon my laptop and there was much rejoicing.

Do you wear the t-shirts that you have designed?
Occasionally – I wear button up shirts to my job on most days but every once in a while I’ll sneak one in.

Have you seen somebody wearing your tee in the real world?
Not yet! Looking forward to it – I’m probably going to hug the person, could possibly be an awkward or even litigious situation. My friends text me with photos of folks they run into wearing my stuff, but I have yet to see it with my own two eyes.


Do you have any role models?
My Father is my number one role model – he’s been a teacher back in Ohio for 35 years. I can hardly imagine doing anything that long, but he continues to find ways to be creative, improve himself and is constantly reading, always challenging his own views on any number of subjects. Having an open, curious mind and being teachable are two of the priorities my parents instilled in me from an early age, and it’s one of their greatest gifts to me.

How is life in New York? Ever feel like living somewhere else or is the Big Apple just too damned awesome?
New York is wonderful because it brings the world and all of its wonderful cultures to you – which makes you want to go out and see those places all the more. Who knows what the future holds though? The Shadow knows.

AAUGH! T-Shirt by Nathan W. Pyle at Threadless
Peanuts inspired tee at Threadless

How often do you eat bagels or hear people say fuggedaboutit?
I am a fan of H & H bagels, while others insist Ess-A bagels are best – but no one ever has said fuggedaboutit to me except maybe ironically.

Does my stereotyping annoy you?
Ha! The New York stereotypes I learned growing up just are hilarious to me now. For instance, I was amazed to see not a single stray dog in three years in Manhattan – that Oliver & Co. flick was completely fictional!


Which two tee designers do you admire the most?
Fatheed (Aled Lewis) – Aled actually forges new territory in the medium of tee designs – which is hard to do given its limitations. And his timeless concepts and illos are as crisp today as they were when he made them years ago. Phenomenal.

D3D  (Leon Ryan) – killer illustrator, master of vectors. I’ve learned so much from him. I wanted to give my designs depth and texture but I wanted to learn to do it with vectors. I didn’t think it was possible until I saw his stuff.

Who would you like to see featured on the Shirt List next?
Ed Hardy


What design trends have made you go WTF?
I can’t believe people send me money for t-shirt designs. That trend is probably both my favorite and surprises me most.

Any advice for other designers/artists?
Don’t give up! Ask for help before you give up.


Are you a dog or cat person?
Dogs all the way.

Website: Nathan W. Pyle
Twitter: @nathanwpyle
Facebook: Nathan Pyle

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3 thoughts on “Interview with Nathan W. Pyle”

  1. That’s my nephew! You rock, Nathan! Now I know what all that Threadless stuff I see on Facebook is, from both you and Gabriel.

    Good work, Nathan. Great interview.

  2. Tom and Mary Minor

    Good interview with Nathan. It is nice to see what my brother is doing!! Miss seeing you! Your other brother, Tom

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