There comes a time in every taxpayers life when he or she “graduates” from the 1040-EZ to the 1040 or 1040-A. If you're not sure whether to itemize personal tax deductions ask yourself this: Are you ready to pass up a tax cut? Because if you have enough expenses in the right areas, you can probably save yourself money by itemizing allowable federal tax deductions. The key is figuring out if your expenses in these categories add up to more than the standard allowance. If you paid mortgage interest, property taxes, medical expenses and/or made charitable donations, chances are you'll come out ahead when filing income taxes if you itemize rather than take the standard deduction.