Just adding my two cents! My boyfriend and I take a funny Christmas Card photo every year, and this year we went with a fifties theme:
To do my hair, I just curled it like crazy, and then pinned it up a little in the back so that it looked more like a bob (my hair is actually more shoulder length). Bobby pins and lots of hairspray helps.
As far as my outfit- the skirt is just a regular old A-line skirt that I had in my closet, but to make it more "fifties", I hiked it up to my high waistline and used a clothespin to secure it in the back.
The shoes are from Wal-Mart!
Also lots of blush on the apples of your cheeks for nice, rosy cheeks.
Hope that helps
Sounds like a fun project.