It seems as though my Pleasure Doing Business skirt goes with anything and everything, anytime and anywhere. It comes in dozens of colors and lengths, but I chose the 5-banded black combo. It is completely elastic, but completely comfortable. At night it looks good with a fitted tank tucked in, but I prefer it with a flouncy top, such as my IRO blouse from Paris, or an Equipment blouse (tucked in or out). I also love it with a chunky loose sweater and tights. My favorite oxford wedges (Shopbop) look so schoolgirl but so adorable with scrunched calf-length socks (mine are from Gap).