I'm with you all the way and I've been wearing dresses frequently and have purchased quite a few for Spring and Summer. This past week, I just ordered an Eileen Fisher dress from Garnet Hill and hope it works out for Autumn and Winter.
To me, there's an ease and a polish with a dress that can be dressed up or down, depending on the shoes, boots, topper, tights or leggings.
From what you're showing, Madewell has a nice selection and I'll take a look. I like them all for different reasons: the black is a wonderful basic that can take on drama with a scarf or other accessories, the grey print has waist-defining interest and I like the loose sheath-like quality of the red plaid one.