I've made more than a dozen iron-on shirts for several members of my family. My mom was just wearing one today and it looks great after numerous washings. If you follow these tips, you will see a difference.
There are 3 tricks to help iron-ons last.
1- If your design does not take up the entire 8.5x11 space, trim them down. For example, let's say your design was on Mickey ears. Don't iron the entire sheet, but trim around the ears to have just the shape. Less transfer space, less crackling. 90 degree corners are more prone to peeling than rounded edges. An easy design would be the mouse ears with each one personalized with names.
2- Buy new shirts and wash them BEFORE you put iron-on the design. All shirts will shrink a little. If it shrinks after the design is on, the design can (and probably will) crack. Unless you buy transfers that specify they are for dark colors, stick with light. Light blue or gray seem to work best. Use bold colors in your design so that they "pop."
3- After the design is ironed on, the t-shirts should be washed inside out and not in hot water. Warm water seems to be ok, cold is best if you can. This is true with any screen print, but more-so with iron-ons.
I have several iron-on t shirts that I've made and have lasted for over a year. All t-shirts are gonna wear down after time. There really is no cheaper alternative. Your only other options will be zazzle through the disney shopping site or going to a local screen print company. The problem with the latter is that they often have a minimum order requirement (often 20+ shirts) to get a reasonable price. I have ordered t-shirts for several of my college organizations, so trust me when I say I have experience with this!
There was a recent thread (maybe a few) on this same subject, maybe try a search for some more answers.
One last thing...if you do the iron-ons and want text....TYPE THE TEXT BACKWARDS. The transfers are designed from the inside out. Be sure to follow this rule or you will end up with backward (or even upside down) text on your t-shirt! You can easily make 10 shirts for under $30-40. Try craft stores like AC Moore, they run specials on plain Hanes t-shirts for $2-3 a piece in all different colors and sizes. Good luck!
