I had a sweat costume last year. One of my attractive lady friends asked me what she should dress up as so of course I replied school girl because I fully admit to having a problem in regards to girls wearing school girl outfits. Anyway, she challenged me and said she would do it if I did it myself. Well needless to say I took up the challenge and dressed in full out school girl, down to thigh highs, heels, a wig, fake boobs, tied dress shirt, etc etc
Now you'd think that dressing in drag would hurt your chances with the ladies but you'd be dead wrong. EVERY girl dressed like a school girl loved it and wanted to dance / take pictures with me. Two thumbs up.
Here are some links if you want to see a drunk guy in a plaid skirt:
http://community.webshots.com/photo/207377575/211121961oDBKbJ
in this one you can see the girl, who ended up wussing out and dressing like a cowgirl but she still looked good:
http://community.webshots.com/photo/207377575/211122066AwFJYW
Yes, my roomate dressed as a giant penis.
Adam