What I ended up finding is the softest, most comfortable freaking skirt in the history of EVER.
It's nothing special - just a jersey cotton skirt from the Gap, but it has the perfect fold-down ruched waistband that gives you just a little bit of control in the below the belly button area. It's fits loosely enough that it's comfortable to move in, but tightly enough that it doesn't blow like crazy in a strong wind. It's pretty damn perfect. The one flaw is that the tag in it is crazy annoying. Even after cutting it out, the little leftover bits drive me crazy.
But otherwise - perfect skirt. Awesome on the weekends, awesome for work. And it's even on clearance! And I'm being nice enough to share this with you all so you can get some too! You can find it in stripes and in solids!
T-shirt - Smart Set
Skirt - Gap
Shoes - Converse