I nominate San Diego as the worst dressed city in the USA. Where shorts and a non stained v-neck t shirt with clean well made sandalls are actually considered to be "too elegant" for most people. It's like the better you look the more people want to start conflict with you. Good training for those with conviction. With that said there are parts exempt from that mentality such as Little Italy, South Park, La Jolla, the city of Del Mar. Encinitas is not well dressed but has really great people that accept and welcome personal style.
Edited by Tibor - 9/25/11 at 7:21am