Wotto—aka Craig Watkins—has spent the last 17 years building a world full of oddball characters, chaotic charm, and stories you can’t help but get lost in. Since joining Threadless in 2007, his detailed, character-driven style has only grown weirder, sharper, and more unmistakably his. When we last spoke in 2015, Wotto was already turning cluttered thoughts into lovable weirdos. Now, with a thriving freelance career, a cast of recurring misfits, and a few art battle scars, he’s leveled up without losing what made his work stand out in the first place.
As Threadless celebrates 25 years of independent artistry, we caught up with Wotto to revisit his early wins, creative evolution, and the platform that quite literally changed his life.
In our first interview in 2015, we talked about how you create cute characters with hints of a darker, more menacing backstory. How has your visual style or creative focus shifted since then?
Craig Watkins: It really hasn’t changed that much to be honest. I think my style has evolved a little and I am more focused on a specific group of characters now. I’m establishing a group of misfits that are more recognizable as my characters. They still have a touch of darkness though.
What’s your favorite piece you’ve ever submitted to Threadless—and what made it special?
CW: The Clown piece, it was a very early submission and I really didn’t think it would win. It had a quirky humor to it and I wasn’t sure people would relate to it. It won and it sparked an interest in apparel for me that has literally changed my life. I was working in a less creative space and Threadless inspired me to rework my portfolio and get back into the art world. The kick in the arse I needed. This win motivated that energy and now I am up to my eyeballs in a creative career, so thank you Threadless.
Has there ever been a moment when you looked at your old work and thought, “Whoa, who was I back then?”
CW: Yes, absolutely. Some of my submissions were total garbage, haha. All artists start somewhere and some are brave enough to embrace their past works. I look back on all of them fondly though because that was my journey. I remember the instant response you got from the Threadless community, that was golden. Both elevating and sometimes humbling.
You’ve always had a talent for creating densely packed, character-filled worlds. Do you ever get lost in your own pieces?
CW: Every day. This style of working was always reserved for my sketchbooks, and I really didn’t think anyone would care about it. It was a way to offload my cluttered mind on a daily basis. A friend encouraged me to share it and people responded to it positively, so I just kept sharing.
It’s weird because back in 2009 when I started this style of drawing, there were only a few doing it. Like Killer Acid, Jon Burgerman and Timothy Goodman. With Mr. Doodle’s explosion onto the scene, the art style has become way more common. Unfortunately many new artists think his success can be replicated easily, I see a new Mr. Doodle every week these days. Artists need to realize that this style has been done now. Find something that sets you apart from this. Something people want to employ you for.
How do you define success for yourself now, compared to when you first joined Threadless in 2007?
CW: Great question. Honestly, it’s being involved in projects I care about. Whether it’s big name brand partnerships, start ups, or just a cool idea. I like a project that inspires me or makes me want to do it because it’s unique or fits my style well. I have bills to pay but I have turned down large name collabs because they just didn’t fit. That’s hard to do. I love the big brand collabs but I also like working with new smaller brands too. They typically give me more freedom and I feel like we are building together. Success to me is being able to pick and choose if I do or do not take on a project.
Is there a non-artistic hobby or activity that surprisingly fuels your creativity?
CW: Music. I listen to a lot of music and it has always fueled my art, and I also like to get out of the house and wander around. I like cities and seeing lots of people—I find inspiration in that. A lot of the drawings I create are somehow based on narratives I have observed.
Do you feel your UK roots still show up in your work, or has your aesthetic shifted with your environment?
CW: My work has always lived in a non specific place, I love the UK and I think inevitably some of it creeps in, but it was never really intentional. I like a lot of my characters to be from no place specifically or any race/gender either. It’s not really important. Some of them don’t even have arms! Their story or interpreted story is what I care about. I like to hear people talk about the characters, “That pear is sad because that ghost stole his hat.” That sort of thing makes me smile because the art is communicating the narratives that played out in my head. I want the viewer to constantly discover things in my work.
Is there a particular moment on Threadless—whether a challenge win, a collab, or fan reaction—that still sticks with you?
CW: Many. The community especially. I know people still today that I met on Threadless. I actually live with one. She’s my wife. We met on the Threadless community section of the website back in 2008. She’s awesome. Without Threadless, I literally would not be sitting in California right now typing this. I owe a lot to you guys.
You’ve been involved in live art battles, toy design, murals, and merch. What’s been the most unexpectedly rewarding format?
CW: The art battles with Secret Walls are incredibly rewarding. The concept is simple: two artists or groups of artists battle on large walls for 90 minutes with only black paint in front of a live audience. It’s wild. It’s a pressure cooker but in a good way. You are often thrown in with an artist you have never met, which instantly creates a friend and a unique piece of art. It’s a brilliant sense of community. I guess art communities in general are very rewarding for me.
What’s one misconception people have about working artists or the creative industry that you’d love to clear up?
CW: Oh boy. So many. First of all, the projected glamorous lifestyles of artists on Instagram. Most of that is BS. I know some artists performing at a high level, and they are in the same peaks and troughs of the art world as everyone else. That reality is rarely shown on Instagram or social media. Success in the art world isn’t measured in money or client lists, it’s measured in the journey and the people you meet along the way. Yes, we have bills to pay, but ultimately I am excited to be in a room of creatives, making a unique project, or working with a brand I love rather than any riches. Don’t believe the hype people.
Looking at the full arc of your career so far, is there a particular milestone that still feels surreal?
CW: Reinventing my art after winning at Threadless. Like I said, it was the kick I needed. Little did I know it would change everything for me on a personal level too. Taking risks, starting over, and leaps of faith have always worked out well for me. I’ve trusted my gut even when some people weren’t supporting me. Threadless ignited a passion for t-shirt design I didn’t know I had. That projected me into all sorts of opportunities.
Are there any new directions or styles you’re currently exploring or itching to experiment with?
CW: My style is always evolving, the more I draw the more I change. I do want to try some more murals and 3D items, I’ve enjoyed working on those in recent years. Unique product types too, they are always fun.
Finally, in the spirit of celebrating 25 years of Threadless, what does being part of this creative community mean to you personally?
CW: Everything. What Threadless built was very special. It connected people all over the world and inspired so many people to create. It launched careers, forged relationships that turn into marriages, and from that, babies! Threadless was what I needed at that time the most. I’m not alone in feeling that way. I’ve met many Threadless folks and they are all very grateful and honored to be a part of the Threadless legacy. Threadless changed my life forever, it’s really that simple. Thank you to Jake and the founding team, the employees over the years and the current team. The people have always been awesome at Threadless, that’s made an incredible difference.
Massive thanks to Wotto for letting us peek inside the beautifully weird world he’s been building for the past 17+ years—and for reminding us why this community still matters so much. His story is a testament to what can happen when an artist leans into their quirks, trusts their gut, and finds a platform that gets it.
Want to bring some of Wotto’s delightful chaos into your life? Head over to his Threadless Artist Shop to snag designs that are packed with color and character. You can also follow Wotto on social media to keep up with his latest work, upcoming art battles, and whatever new misfit he’s drawing next.
