Experimenting with prints is always fun! Luckily for me I have a mom who kept her bomb wardrobe from the 80's and an obsession with wearing shirts as dresses. If you're going for crazy patterns try a solid colored shoe to balance out the confusion. During the winter oversized sweaters do the trick also, even if it means browsing the men's department for you "imaginary" boyfriend.
Note: Make sure the "shirt dress" is long enough to cover all your assets. Keep it classy ladies. *winks*