I had such a blast making this for my dad - and excited to send it to him too. I did encounter a bit of trouble when I was making this, but I found a solution to share with you guys who are planning to make this for your awesome dad!
This is one of the reasons why for me it's so worth it to get a Silhouette machine - I love making custom HTV shirts and hats and what-have-yous. This one I designed for my dad going for a top-gun-ish effect, and I believe I did get it right. Oh yeah - I forgot to tell you, you can download a free template you can trace on the tutorial page as well.
So if you are interested in learning how I made this AND to download the free template, head on over to Craftaholics Anonymous by clicking any of the photos above or the link below - happy crafting, guys!