For my Dad's 60th birthday, we just had to take advantage of the fact that there was a family surname joke and a Mr Men vacancy that matched up.... We made a personalised T-shirt!
We sat down and tried to draw a cartoon of my Dad as a Mr Man, and in the end took the best bits of both to create the B&W version of the fella to the left, which does kind of look a bit like my Dad! We outlined it in black texta and scanned it in (hint - use the smoothest paper possible so no paper texture is scanned in too). We tidied things up on the computer's basic paint program, block coloured bits in, then added final detail such as the lines below for the ground. Lettering was added in a style most like that on the actual books. In the version that went to Dad, "Mr.Merry" is holding a glass of red wine. The picture above is a kiddy version for my son.
Bought some T-shirt transfer paper from computer store, and printed the image in reverse, then cut out and ironed onto our t-shirts! We did a test run (revamped an old t-shirt with quick graphic ironed on) but weren't very happy with how it turned after being washed, despite following instructions. Might get a special t-shirt printed professionally, but for the timebeing, many t-shirt makeovers are in store using the left over computer transfer paper!!