Air conditioning for an excessive sweating disorder, a nose job for a wine taster -- bizarre deductions like these are likely to spark suspicion from the IRS. But don't let that stop you from claiming them if they are legitimate. Both the nose job and the air conditioning unit were allowed, for example.
But others, like used underwear donated to charity or medical bills for pets, were not. So don't stretch the limit too far, and when in doubt, ask a tax professional before turning yourself into a target for the IRS.
