The gingham "Studio Sweetheart" dress from Mod Cloth has a nice 1930s style and a comfortable shape.
Even so, it's not an outrageously cool dress. But wait! There's more.
In addition to sleeve shortening epaulets, there are strings underneath the dress that allow you to shorten and balloon the hem. So cute and fun! It reminds me of the Homecoming Queen Skipper doll I loved so much as a kid.* Do I want to pay $140 for it? That's a bit much even considering that it's two dresses for the price of one; however, I will certainly be watching for it to go on sale throughout the season.
*She wasn't well loved just because of her awesome dress. My 17 year-old-brother spontaneously decided to buy me, his 5-year-old sister, that doll with his allowance money for absolutely no occasion. It blew my mind then, and I still have no idea why he did it. (He is a miser.) When she broke years later, I cried and blubbered like the world was over.