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I used to sell 'indy fashion' shirts in omaha all the time that I made. I would just buy $2 nightshirts (emo tight ribbed cotton shirts) and spraypaint stencils of Tom Delay on the back at an angle, with Krylon. Then sell em for $25. The krylon could be washed forever and not fade.
But on a jacket just make sure you use a latex based paint because that will break down/melt the artificial fibers of your jacket.
I saw Anthony Bornowski had a city skyline stencil and did it on one of the rolls of a puffy jacket. It looked pretty cool. If you use cloth paint and do it on a small area it should be fine.
yeah i know a kid that sprayed his snowpants and like custom painted them and put some clearcoat over it and it worked fine and turned out pretty dope. make sure you dont cheap out on the paint though or get dabric paint maybe and get a clearcoat