It is my rough experience that when people say 'Nice Shirt/Tie/Jumper', at least half the time what they actually mean is 'That shirt is ugly, but distinctive'. They first register the need to comment on the odd-looking thing, and since 'your shirt is crap' is not polite, you end up with 'nice shirt'.
For some reason, the expression 'I like that shirt on you' doesn't ring quite as false. It may well be motivated by the desire for false flattery, but that is a much easier problem to deal with. For starters, it's unlikely to lead me to wear an ugly shirt too often because someone once said something nice about it.
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