My boss told me today, after commenting on my poufy, pleated "potato sack" skirt and the appearance of my ass in said skirt as opposed to the actual size of my ass, that he'd like to see me in jeans, a wifebeater, and cowboy boots. Inappropriateness aside, it sort of made me want to go shopping. So, obviously, I went out and bought a skirt at American Apparel. It's superswingy and cute. I'd advise sizing up so it can hang a little lower than Dov Charney (and probably my boss) would like.
American Apparel natural denim circle skirt, $45. It also comes in fun salmon and "blueberry" blue (basically unnatural-denim blue).