I think you were asking the guys specifically plus I think that you have received a lot of great answers too. I liked LFL's and mrscac's especially!
That said I will still throw my two cents out there. I think you really should look inward and figure out what message you feel want to send with your clothes. If you want to project a sexy, individualistic personality out to the world, that's great. The only thing I would wonder is whether wearing a 15 year old's outfit really sends that message? On the other hand maybe you want to send the message that you like youthful clothes and are hot enough to carry it off (like mrs cac, I say great :)), then go for it!! Just be true to yourself and I think you'll feel great.
It's funny but when I see older women wearing youthful clothes there seem to be 2 camps. Those that seem like they are trying too hard and trying to desperately hold on to their youth and there are others that seem relaxed and natural with their clothes. There just seems to be an attitude with the clothes, makeup and hair that send that message. My 84 year old grandmother seems to balance out the old woman stuff with a natural relaxed youthful look. My friends always comment how chic she seems. She has fine thin gray hair that is cut extremely short. Doesn't wear much makeup except for a splash of red lipstick. Still wears high heels that aren't the shoes a 20 year old would wear but certainly they aren't old lady shoes! Somehow she always looks youthful and fun while looking COMFORTABLE with herself. AND I think that's what you are really looking to be - a woman who is comfortable in her own skin. Am I right?
I go through similar thoughts about my clothes and what statements I want to make. My message I want to send is different than yours but I am still struggling with defining that message and then taking the time to shop for the clothes that will send that personal message. I hate to shop so the shopping part is more difficult for me. Plus finding what I want is not as easy for me so shopping can be irritating.
Anyway, as far as guys I think you'll probably find a wide spectrum there. My Boyfriend in high school hated mini-skirts and not just on me. He would point out one of the hottest girls at our school and say "See how awful that looks on her"? Weird I know but everyone has different taste. (I still wore mine anyway!) Some guys may not even notice the clothes but just see you while others might be distracted by the clothes. That's why I think it is more important that you feel good and happy about how your clothes reflect your feelings.
But what is happiness except the simple harmony between a man and the life he leads? ~Albert Camus
