Crazy Sounding Tax Deductions That IRS (Or The Tax Court) Says Are Legit | Forbes

Are you searching high and low for tax deductions? In the run up to April 15, you aren’t the only one. Unfortunately, it is too late to date checks December 31, 2015! Since taxes are annual, you must think about last year, 2015. Still, if your facts are right and you feel adventurous, here are some unusual deductions taxpayers managed to get approved. Admittedly, some had to take the IRS to court to get their deduction approved.

Cosmetic surgery costs are usually non-deductible, but an exotic dancer named Chesty Love tested this rule. If you want bigger tips, you go bigger, she reasoned. So she decided to go way bigger, shelling out for breast implants that would bloat her bra size to 56-FF. When she wrote off the bill, the IRS said it was nondeductible cosmetic surgery. But in Hess v. Commissioner,the Tax Court allowed tax benefits, allowing her to claim the implants as depreciable assets, a type of stage prop.

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