Pockets! Yes!
Dunno how much chalk you use. When I taught about a million years ago I found myself wearing a lot more lighter neutrals because black would pick up every speck of chalk dust.
It's going to get too cold for these soon, but when the weather gets warm again, is it possible to wear capri pants? The kind that go to your high ankle/shin, as opposed to just below the knee. I've found just having a few inches less fabric has made a huge difference in terms of how hot I was over the summer. Should be sales on that now, too.
I like both tops you showed earlier, and that's a great skirt. One suggestion is a few good basic skirts and pants, that go with a lot of things, then mainly concentrate on tops and accessories. Black pants and skirt, grey pants and skirt, tan pants and skirt, okay, you've got enough for any given week with an extra for laundry, so then start working on tops. Navy is another good neutral but every company seems to have its own idea of navy, which technically is supposed to be close to black. Every company also has its own idea of tan and grey, too. Tan can be light and lineny or it can be almost khaki, and grey can have elements of pink or blue in it. Grey is supposed to be hot this year.
With your complexion and hair and eye colors I'd go with a
Spring's color palette.
http://www.thesoko.com/thesoko/article742.html You might be able to get away with some Autumn and Summer colors, too, but Winter (start whites and blacks, clear reds with no hint of orange, and a lot of plums) might be a little much. Here's another link:
http://www.beauty-and-the-bath.com/Spring-Color-And-Skin-Tone.html