Hi, Brian - to do exactly what you're asking about is a huge investment of time and money. You need a machine that can embroider hats and the special hat hoop. You also need digitizing software. The machine companies all have their proprietary software which is usually very expensive (at least $1000), and there is also a program called Embird that is much more reasonably priced, but you'd have to purchase the digitizing add on. Then you'd have to learn how to digitize. I haven't done much but I've done enough to know that I don't want to invest that much time in learning how to do it. I think you can upload an image then tell the software to digitize it, but then you'd have to tweak it to get it just the way you want.

If you just want hats for your softball team or something like that, your best bet is probably to just have them made by someone who is already in the business. Just make sure you don't have a copyrighted logo, or that you have permission to make copies of it.

Donna