The thing about CDHagg's fits is that I always get the vibe that he's wearing those items because they're the only ones he has. Like, if he's wearing black lace-ups, they're his only pair. If he wants to wear a blazer, then he's got just that one. As a result, nothing really meshes together- it's just a facsimile of a fit he's got in his head.
I'm not trying to knock people that can only afford one of each kind of item (though I doubt that's him since after all, he has an espresso machine and enjoys opera) but it often looks like instead of wearing the item that would go best, he wears what he's got that's the closest thing to it.