I have a terrible time with dresses, too, Karie, and I tend to wear only shifts as a result. I seem to have the same build as Ummilla: rectangle, small chest, wide waist. Ummilla likes elastic waists, and I can see why -- she looks fantastic in that photo she posted. But for me, shifts are the only style that make me feel modern (odd, since shifts are so retro!). Typically I avoid dresses -- and skirts too, since they are SO hard to fit. I wear a lot of pants.
But when I find a shift, I wear the heck out of it. I just bought one on sale at Anthro and it worked beautifully for an occasion this spring. It's longer on me than on the model, it's silk, and it's easy. Not sure how you feel about shifts but I love this one.
http://www.anthropologie.com/a....._-SUB_CATE
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