This blog entry has some great tips on how to wear a maxi skirt. I bought one. Best investment ever. It's basically yoga pants in skirt form, looks chic with just about anything, and fosters the illusion that I actually put effort into dressing myself.
Pair solid or neutral tops with patterned or brightly colored scarves for a pop of color to polish your outfit ... so simple and classic. A new look everytime you change your scarf or boots or accessories.