Okay -- Ummilila and Una, better talk to Greg about that stuff.
He is a genius and will fix it.
Karie, it is not YOU. It is the DRESS.
As a fellow slim hourglass/ rectangle, here is my secret, that is really no secret:
HIGH NECKED SHEATH DRESS.
Get it in jersey and if there is ruching of some kind, all is forgiven.
Seriously.
You probably don't want something as dressy as the Nicole Miller, below. But there are lots of similar dresses out there in different fabrications. The Kamalikulture ones come to mind. Those ones are cheap as chips (as Angie might say) and pack like a dream!
But if the shape just feels too dressy, no matter what, well...I don't think fit-and-flare is completely out...I just think it is trickier. For me, personally...a part of me really loves a fit-and-flare style -- it appeals to my girly/ pretty side. But I do find them awfully awkward looking on my angles. I can get them to fit my body, but they seem to argue with the rest of me, if you know what I mean.
Still, I've seen you rock that silhouette, so if your heart is set on that shape, how about that great Halogen skirt that Angie sported in the spring (if still available) with a top tucked in?