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It's important to look good, but its also important to not look like your trying too hard. I think for you, wearing tight clothing would qualify as trying too hard.
That's a terrible stereotype to try and push onto him, he may look amazing in tight shirts, and by you saying that you could have just put him off them. Wearing tight clothing is a hell of a lot better then wearing loose clothing as long as you have a decent body, if you don't, act as if you do. Feeling positive about your body and your appearance has the greatest effect on the people around you, and that will make the difference between them thinking 'He's trying too hard' and 'He looks amazing.'
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Ultimately, it does boil down to comfort, but it also depends on what kind of girls your trying to attract.
This is the best thing about the post above, it does boil down to comfort, it boils down to whether or not you're comfortable with your own body and what clothes you're comfortable in.
If you feel negative about your body, then work on it, set yourself a work out schedule and get yourself to a stage where you like you're body. Eat well, exercise, and live well, It'll give you more energy and you'll have ALOT more fun.
As for clothing, if you don't feel comfortable with you're body, you can wear dark colours which will allow you to look slimmer and leaner, or you can layer, which is a great way to look both stylish and attract attention.
For further fashion tips, you can check out KinoWear
http://www.kinowear.com/blog/category/style-tips/
Good Luck man, and remember, you're only as good looking as you believe you are
