@Scoresby suggested we give a few-of-a-kind physical prize to long lived cowboys that can't be acquired by other means. Depending on how the print goes, I think they'll be snapback cowboy hats (like a trucker hat and a cowboy hat had a hat baby):
I also did a low volume run of beanies. I made a spec beanie in the past but was disappointed in the size and quality of the beanie itself and the size of the embroidered area. I found a company that prints on Carhartt beanies and is willing to do a big embroidering (and hopefully I can cut the Carhartt label off).
Oh, and a single digit run of embroidered corduroy hats in case the cowboy hats don't pan out: