We played "Cool" or "Not Cool" with Chicago etiquette expert Leontina Richardson who weighed in whether or not it's OK to wear shades of white to a wedding, if stylish flip-flops get a pass for special occasions and if thong bikinis are always a no-no.
For more on Leontina and Stepping into Technique, visit: http://www.steppingintoetiquette.com/