Damn, I love a good n' messy/casual/dressy style. If your man has stylish friends that are incredibly good looking, maybe ya'll could pull some styling like this off. I'm digging the second one to the right. Imagine him buttoned up, with a little corsage. So hot.
On the other hand, they kinda look like an older Jonas Brothers boy band so PROCEED WITH CAUTION!
pic from NK Stil