If you spend a lot on deductible expenses — such as mortgage interest, state and local taxes, capital losses, medical expenses, or donations to charity — you might be able to lower your taxable income more by choosing itemized deductions over the standard deduction. If your deductible expenses throughout the tax year were lower than the standard deduction, you should take the standard deduction. No, if you deduct property taxes, you can't claim the standard deduction, as the property tax deduction is itemized on Schedule A.