Before Christmas, I said I would post with the results of my quest to make chef pants with pirate flag type skulls on them, so here we go. I wound up buying black pants and stenciling the skulls.
( photos )While I enjoyed this as an experiment, and I love that the recipient likes them, I am not sure I'd recommend this project to anyone else unless you don't mind the fairly time consuming process. I used speedball screen printing ink, which must be heat set for 3-5 minutes on each side of the design. 3 minutes x 9 skulls x both sides = 54 minutes of ironing. Each skull must be stenciled separately, of course, so you can't do the entire garment at once. Although if you have a large craft table (which I don't) maybe you could do several at a time.
One issue that I encountered was the progressive degradation of the stencil, which I had cut into a fairly thick piece of transparency film. The first five stencils look great. Crisp outlines and so forth, but after that the spray adhesive and paint built up around the edges, making crappier prints. If there were going to be a next time, I would cut two identical stencils. Hopefully you can see what I mean in the photo of the stencil itself.