The summer dress (as also mention here!) is the easiest thing to transition from most seasons, so I have no qualms with half my closet being hangers full of them. A newer one that I've already worn a few times for both the versatility and comfort is this athletic inspired dress.
What's better is that they go perfect with my second pair of Birkenstocks that I just had to get for three reasons, 1) I absolutely LOVE my first pair that are black; 2) These ones are in narrow - so actually fit a bit better than my original pair, which I have learned are a bit of a wide fit naturally; 3) They are on sale.
As you can see below, this dress, and even those Birks that are all too comfortable to retire anytime soon, will easily transition into fall with the addition of a jacket - and I love that simplistic look! It's all easy - and pulled together with a red pout, of course! ;)