On a guy, it really depends. I agree that it's easy to end up looking like either you should have known better or you're trying too hard, but in the right climate and with the right cut, I think it can look really good.
Admittedly, though, most of my ideas tend to involve layering something sleeveless (like a hoodie) over something with sleeves.
Admittedly, though, most of my ideas tend to involve layering something sleeveless (like a hoodie) over something with sleeves.