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I have a good $100 tailored men's suit I bought from K & G. I only use it to go to job interviews, otherwise if I go around wearing it I feel uncomfortable feeling overdressed. I'd rather wear casual wear. But me being a crossdresser too I love going out decked out in a nice skirt suit! I feel beautiful, not overdressed then.
I really like a guy who can rock a button down with jeans, a leather belt and loafers, relaxed but pulled together. I also quite like the looks put out by Esquire, GQ, etc. men in those magazines look very sharp without looking uptight. However, guys can look cute in a hoodie and cargo pants too. Its all about the total package. A laid back demeanor and a general air of friendliness go a long way. If youre freshly showered and follow good hygiene, anyway!
Other--in jockstraps. LOL, jk!--on a more serious note, probably well-dressed.
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