I don't like to reinvent the wheel; If something works stick with it. I made these hipster rabbits back at Easter time, and the concept worked well with pumpkins.
I did some research on Pinterest on hipster pumpkins. I took the parts that I like (glasses, mustaches, and bow ties) and created some drawings. These pumpkin cookies can be made using any pumpkin cookie cutter you have. I started out by piping sections onto the pumpkins. Then I flooded the two outer sections. Once the outer sections dried, I filled in the middle section. I piped on the black faces after the orange was dried. The next step was adding the hipster details. Finally I added a green stem.