Wearing a long skirt with sneakers gives the look some coolness. I have never been a flat gal, converse were always my thing so I would wear them with everything and everywhere. I remember the first party party ( like dancing and all ) I ever went to, I wore a short skirt and my favorite converse: the red ones. If you are going to wear high waisted skirts I believe thin sleeved shirts give it a greater enhancement.
Take care kids. Gaby Calix