Being nice to use would be the top priority, i'm buying these for my brother, who's only used buds before, but these would both suit his needs, due to being used on loud bus's.
Actually, I'd recommend the Creative EP-630, which sounds just like the CX300 at a much lower price and with a more manageable Y-style cord (as opposed to CX300's behind-the-neck J-style). I've found the comfort to be great as far as semi-canalphones go.
I have tried both and ended up going with the CX300. To me, it has better bass and midrange. It also blocks out enough noise for public transportation. A good overall choice for your brother.
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