When I wear attention commanding clothes, such as plaid jacket, or unusual colored pants (mustard, pink, aqua, purple), my usual test if it works is whether I receive at least three complements in an evening. I have a crean houndstooth Dior jacket that pulls in about 5 or 6 complements each time I wear it. Its not uncommon for guys or girls to want to take their picture with me. Several times guys have asked to borrow a jacket or a hat so they can be photographed in it. This has affected how I dress, I'm not sure how it plays out on a date for me to receive much more atttention than the girl. Only once did I receive a complement from a gay guy trying to score. Being very well dressed in a more conservative mode doesn't generate the same response, I think because you are doing something well that people expect. My Berlutti shoes have never been complemented, but I have some alligator, whole-cut Edmond Allens, and spectator shoes that have been complemented on. Of course, this is the San Francisco Bay Area and most guys dress like they don't care. Girls do a bit better.