Have you ventured into the world of Freezer Paper Stenciling yet? I've had a roll of freezer paper forever with a list of projects, finally tried it and am addicted! For our preschool co-op I decided it would be fun to make Jack-O-Lantern shirts, especially since our theme today was pumpkins!
MADE has a great tutorial on this technique. I'll just add a few tips on how to make it Toddler Approved!.
Be sure to wash, dry and iron your shirts before starting (if you're curious, these long sleeved orange shirts were found at Wal Mart for $3.50). Create a jack-o-lantern template (see below for my example) and trace it onto the freezer paper.
I recommend using a generous amount of freezer paper for each shirt if you are planning on letting your child help paint. With shiny side down, iron the freezer paper on to the shirt.
Place some newspaper or cardboard between front and back of shirt (I found that cereal boxes were the perfect size). If you are working with a small number of children or have a few assistants with a large group - I would suggest using fabric paint and brushes to color in the stencil. If you have a bigger group, limited amount of time and are by yourself (which was my situation) spray paint works wonders! I'm pretty sure that you can actually buy fabric spray paint - but I have been using regular spray paint on shirts without any problems/fading - and it dries soooo fast! Fabric paint takes about 4 hours (or more) to dry, spray paint takes about 1 hour.
If you are using spray paint I would suggest doing it in a well ventilated area, and tucking the sleeves of the shirt behind the back of the shirt so that the spray doesn't get on them. If you think I'm crazy for letting 3 year olds spray paint - there was a controlled method to my madness. I had them hold the bottle and direct the direction of the spray while my hand/fingers had control of the nozzle and flow. This worked beautifully and I am happy to report that no clothes/hands were stained in the process. We hung the shirts on the clothesline, and they were dry in time for everyone to wear their shirt home.