Jen, I love that graphic black and white stripe on you! The dress might be a little wilted from the heat, but the design looks amazing on you. I also love your version of *le safari*. You look cool and collected here, and the open, belted shirt looks a bit like a jacket. That would totally be appropriate in an office here in summer as well. Do you find that knits are hotter than wovens? There are months when I just cannot bear to but a cotton cami on under anything, so my shirts have to work on their own. I like Beth Ann's idea of a shirt dress too. And yay for unlined, washable jackets! They really save the day. I am saving my clothing money for my dominant summer. You're right, the clothes really do take a beating when you're washing and wearing them that hard for so long.
Aside from dresses, I think it makes sense to buy *pieces* like you have on in outfit number 2, all in your color palette that will mix and match together. That way if something's in the laundry, you could grab another blouse and it would match your pants. Last summer I started going nuts with prints and different vivid colors and I ended up boxing myself in a little. Not everything played well together. I hope to avoid that this year.