QUOTE (Strife Idz @ Aug 18 2009, 04:30 PM)

Simple. He doesn't want to look like his father. He spoke about this in later episodes. He really dosen't want to be reminded of his father, The Great White Fang of Konoha. Other than that, he's just another skilled Jonin wearing a mask.
I think it has more to do with not being compared to his father, also because the majority of the ninja world sees The White Fang as a failure. I think that's how started the always wear a mask thing. Now is just his trademark. But it's also obvious he's incredibly handsome by the dreamy expression on whoever sees him without a mask. I personally would love to be in a dark alley with a maskless kakashi...

yes, I know I'm terrible. So sue me!