after standing in front of mirror trying on skirts to keep or toss, I am finding shoes and heel height have a lot to do with the ones to toss or not. for instance a flair black skirt that hit just below my knee didn't work standing there barefoot, but when I put on the heels I really liked the look. Then I tried it with flats, and again, for me it was a no no. also my 2 summery maxi skirts look best with flat sandals-and did not work with the wedgie sandals, although the color is perfect.
I am thinking maxi skirts or dresses in wintery colors and fabrics will look great with boots-if the boots are high enough not to show leg when sitting. I think this would be a great look, especially with low heel boots.