I totes understand about being lazy. I wear skirts and t-shirts 99% of the time, mostly because finding nice pants or jeans that fit sucks. But I wear them with hiking sandals in the summer, and ankle boots, or hiking boots, or converse-style sneakers in the rainy season.

When it's cold, I trade in my running shorts (worn under the skirts!) for tights and knee socks. Layers = good.