R.G.
I would take the messy look now that a teen needing to express them self. Let him develope his sense of style now than later. Not to say he won't try odd things. What is it say to him relationally? What he likes is something you don't like? Maybe you won't like him. What if this sends a message that you would be happer with him if he dressed like some else and you are unhappy with him? Would you want the behavior with out the heart? Would you rather him be unhappy if it meant you would be happy?
Me: Mother of two 17&13. I have wonderful kids I have gone through every color of hair, mohawks, bright green hats, mis-match everything. I have their hearts. They are respectful, thoughtful, caring, fun, loving, bright, wonderful, creative, talented, just to mention a few and I get compliments all the time on how well they get along. I have bondries on modesty and special events.
Hope this helps...