I wanted to make an icon set that could set up a cowboy-styled scene. The scene I ended up wanting to picture was a cowboy under the stars by a fire, resting from his day of work. I used twelve icons to reach my goal. 
My initial sketches were mostly tailored to finding which images I thought fit the best into the picture I was trying to capture. I also experimented with some other images I did not end up liking as much as a campfire scene. Sketching also included placement of the images in relation to each other how they could best interact while being separated, and how I could create the cowboy character without any person. 
My first draft covered all of the images I wanted to make. The feedback I received can be chalked up to two main things, those being that the icons were inconsistent and often lazily done. 
Back to the drawing board, I tried to work on sketching more specific ideas to unify the icons more with each other. The hat and the boots of my first draft were the most well received, and I also enjoyed them the most, so I tried to find a style that suited them. I did more research on how things really looked, rather than trying to make things based off distant memories. Some things I simplified, others I added detail to. The style I was going for was a generally pretty blocky style, using a lot of straight edges, but not discarding curves. 
I think the final draft managed quite well the idea I set out to achieve. Using twelve icons, I managed to set up a sort of scene that is generally, even if not specifically, understood by those who view it. 
Cowboy Icon Set
Published:

Cowboy Icon Set

Published: