I rarely dress up, though if I ride to work skirts/dresses take up less room than jeans in my bag.

When I do dress up b/c of need, it's usually b/c my music kids have a performance. Which means that I have to be "dressier than normal" but also comfortable to stand outside in Colorado in February-April to instruct while they rehearse and warm up for the show. So "dressy" tends to be a wool skirt (my favorite is about knee length and has some flowers embroidered on one side), leggings, and flat boots over wool knee socks. Pair that with a warm sweater and the nicest winter coat I have that somewhat matches.

I don't think I own hose. I almost always wear knee-high boots with skirts, and most of the time I just wear leggings (though sometimes tights) - since only my knee really shows between the two. Most of my skirts are A-line and cut just above the knee. My favorites are usually Ann Taylor but some of their stuff is too old for me.