Greek Week is a huge dance-off that my university puts on where each greek organization choreographs a themed dance for the members, who perform in a gym full of spectators. My sorority's theme was Alice in Wonderland – or to play off our name Alpha Chi Omega –Alpha Chi in Wonderland. We needed a t-shirt design that represented this in a simple, timeless, and cool manner.
It took a while to think of the design. I played around with a whole bunch of Alice's, mushrooms, and Mad Hatters before finally deciding on the Cheshire Cat. I worked in Adobe Illustrator to individually draw the letters to fit the cat's mouth, and once I did I loved it. Initially I wanted the lines to be more ragged, but that design made the words hard to read.
Next, the design needed something else. I tried adding eyes, but I didn't love how it looked. Instead I added whiskers and a nose which I liked a lot more. Take a look at the progression of the entire design below.