According to most people I have a horrible fashion sense. I really do. Loose fitting jeans, t-shirt, and old worn out shoes are all a part of my daily attire. I don't shave regularly either and I have bad hair.
I used to have to dress up on a daily basis when I was a photographer, but normally I dress to what the code is made at my current employment. I'm of the philosophy of comfort over eye candy.
I've learned recently that a lot of what I wear is not pleasing to the feminine eye. Jean shorts are apparently a huge faux paus and pants that used to fit 45 lbs ago no longer look good. Also double breasted suits are not attractive, which sucks cause I was under the mistaken impression that it was the only thing that made me look even somewhat cool.
I found an article that was interesting if not obvious. It's a guy who talks to four women about the state of men's' fashion and the shallow dos and don'ts. If you want to impress your girl I guess you have to read the article. I wish you luck in your quest to find the correct attire. God knows I'm sure as hell confused.
"Every generation laughs at the old fashions, but follows religiously the new." - Henry David Thoreau
A Look at Guys Fashion