I would think he is adventourus, brave and interesting. Go for the formal look (grey, dark colors). What type of shoes are you planing to wear ? This is a key point for a guy. Don't try to make a gender statement, just try to look cool and you will get the right type of attention. You have to shave your legs and don't use fancy pantyhose, just stick to tights or nothing.
Well skirts in general were created for women. Doesnt really make a difference if it has flowers and lace or not. Personally, I really don't give a sh*t what someone else does with their life as long as you aren't hurting anyone. I feel the same with being gay or whatever. It isn't my business and everyone should try and find their own little slice of joy in life. I mean I think its weird...but whatever.
Now if you are asking if I would ever date a guy that wears a skirt, I would say absolutely not. No way.
errrr... ok... it would be a little weird but if that made him happy then ok... I person should always be happy even if other think different... so yeah it would be every weird but if that is what you are into then knock yourself out... :)