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.