You can have calligraphed envelopes, according to this brilliant shortcut from Jenn over at With This Ring...Comes a Lot of Hard Work!
You should check out Jenn's blog to see just how she did it, but basically she used her printer to print addresses in a fancy font, just slightly darker than the color of her envelopes, on the envelopes. Then she traced over the printed type with a calligraphy pen to give it that hand written feeling.
Super cool idea! My handwriting sucks, and Mr. Barefoot's is no better - after all, we're academics, and we're not supposed to write clearly :) But printed labels are ugly, and there's no room in the budget to pay someone to do all the envelopes by hand.