For many taxpayers, the question whether to itemize is akin to a rite of passage. As our lives become more complicated financially, and ideally, as incomes rise, the option can become more attractive or beneficial.
There are some basic rules that apply to help answer the question.
If you had significant payments for medical care, charitable contributions, mortgage interest, taxes or other deductions, they can help reduce taxes when itemizing.
The total spent in these areas should add up to more than the standard deduction to achieve a benefit from filing the long form, the 1040 and Schedule A.
For this filing season, the standard deductions are $5,700 for single filers, $11,400 for married filing jointly.
For the head of household, the standard deduction is $8,350 this year, and $5,700 for married people filing separately.