I know there’s a thread that covers the ground rules of the derby, but I thought it might be interesting and valuable if some of the designers that have been around a while shared some tips with newer designers. Hopefully this isn’t presumptuous on my part, but it took me months of stumbling before I got my first shirt printed, and if there was some depository of derby tips it might have made the experience much easier. I don’t claim to be an expert on anything – I feel like I’m still learning myself – so just take my tips with a grain of salt. This is just what I find works for me, and I don’t even use them all the time. Feel free to offer up some of your own. Hopefully we can keep it positive?..
Look around Check out sites like Threadless and Design by Humans. They have a different fan base and often print different styles than woot does, but you can really pick up how a design works or doesn’t work on a shirt. I’m not suggesting find someone else’s style and copy it, just look at how they present their ideas on a shirt. I come from a concept art background, and that doesn’t naturally translate to wearable shirts. Looking at how others do it really helped me figure out how I could as well.
The First Idea that Comes to Mind Every now and then that first idea is derby gold, but most of the time, for me anyway, it’s the same first idea that everyone else is having. Years of watching the same TV and Movies, reading the same books, hearing the same jokes, means that when we get a theme we probably have very similar things come to mind. When I get those initial ideas I try to decide “is this actually going to be a unique design, and if not can I somehow make it unique?” Usually the answer is no and no and I try to move on to the next one.
Connect things When I’m coming up with ideas I’ll often get random things that relate (or sometimes don’t relate) to theme but aren’t really a working idea on their own. Once I have a bunch of these things floating in my head I’ll start to put them together. Many times these random things will just click so naturally you’ll wonder how they were never put together before! Then check the Internet to make sure they were never put together before.
Sometimes Less is More Personally once I get a concept in my head I try to think of how I can get it to it’s simplest visual form and still get the idea across. First and foremost I think a good shirt reads immediately when you see it. There are exceptions of course (many shirts are a pleasure to pour over and enjoy), but you generally should be able to get the concept within a second or two of looking at it. As an example when James Cho and I collaborated on The Butterfly Effect, my initial idea for it was a very convoluted A to B to C to D to E type of process. There was even a drawing of a sneezing gazelle in there, much to my shame. James wisely advised distilling that concept to it’s essence, cutting out all the unnecessary fat. The result was a much more effective design.
Plus it Once I think the core of the idea is coming across, I then try to think of ways to ‘plus’ it. Plussing is when you have something that’s already good, but now you can add that little extra something, like a visual gag off to the side that compliments but doesn’t overpower the main idea. Some designs don’t call for plussing, but if you can work it in, I think it really helps win over that on the fence voter. 
Let the color limitations work for you It can be frustrating to only have 6 colors when you need 12, but one of the cool things about working with a limited color pallete is that the less colors you use, the more impact the final image will have. It’s one of those inverse proportional things.
Don’t get frustrated My first designs (and some of my current designs, lets be honest) were bad. Really bad. Looking back I can see just how bad they were. But at the time I thought they were something special and couldn’t understand why no one else thought the same. It was easy to get frustrated with the voters who weren’t voting or the designers who were getting the votes. The bottom line was I just wasn’t designing shirts people wanted to wear. I had to either keep doing what I was doing or try to find the area where what I wanted to make and what people wanted to wear intersect. One thing I’ve learned during that process is that being too hard on myself or taking it out on other people gets you no where. Just stay positive and move forward.
Ask for Help/Advice/Critiques People are usually more than willing to share with you some design tip they know or a process you really like, but some will only do so when prompted. Prompt! Also don’t take critiques personally. Most of them aren’t meant to be. We all make mistakes, overlook things, or just can’t step back from a design. An honest critique is a valuable way to get a design to that final level of goodness. Also know when to stick to your guns. If you try to please everyone you’ll please no one. Sometimes people will suggest things to change just because they think they should. Know when to use and know when to discard advice.
Well these are the things that I’ve found helpful in shirt designing. Hopefully someone can use them somehow. Feel free to add you own and try to stay helpful?..
Also, enjoy this Krampus egg.