The initial design process starts with researching robot character designs and skeletons that I know of and creating a drawing based on that research. I immediately thought of the simplified skeleton robots of Mega Man, both Skull Man and Doc Robot. Warhammer 40K's Necron army of Robot Skeletons was also an inspiration in my design process.
Next I started doing various shape designs of possible Skull Designs. Luckily, about a year ago I attended a Still Life Drawing Workshop at AFA Gallery in Scranton, PA, where I remember drawing a fake skull that was part of one of the still life's. My memory of this session aided in quickly constructing these skeletons on the page.
At this point, I was looking more at the Necron Army for body construction of my designs but also utilizing the simple spherical joints from the Mega Mans for the connecting of their robot bodies. I also started gradually adding Pirate attire to my Skeletons. First, adding hat's then researching more and adding some clothing.
I got to a point in the design where I had a very generic Robot Pirate Skeleton and wanted to create more distinct characters from that mold. I started adding sharper edges on their chins to indicate beards, sharp teeth, missing teeth, and indicating hair. Then I started doing tons of research on Pirate costumes, accessories and weapons.
In the final designs, I didn't want to add too much clothes so I modified some of the parts of the legs and arms so they almost look like they are clothing instead of skeleton arms or legs. I also combined traditional Pirate weapons with Power Tools in some of my designs.