Should I itemize?

You should itemize deductions if your total deductions are more than the standard deduction amount. Also, if your standard deduction is zero, you should itemize any deductions you have if:

You are married and filing a separate return, and your spouse itemizes deductions,
You are filing a tax return for a short tax year because of a change in your annual accounting period, or
You are a nonresident or dual-status alien during the year. You are considered a dual-status alien
if you were both a nonresident and resident alien during the year.

NOTE: If you are a nonresident alien who is married to a U.S. citizen or resident at the end of the year, you can choose to be treated as a U.S. resident. (See Publication 519, U.S. Tax Guide for Aliens.) If you make this choice, you can take the standard deduction.

You may benefit from itemizing your deductions on Schedule A (Form 1040) if you:

Paid interest and taxes on your home,
Had large uninsured casualty or theft losses,
Made large contributions to qualified charities, or
Had large uninsured medical and dental expenses during the year,
Do not qualify for the standard deduction, or the amount you can claim is limited,
Had large unreimbursed employee business expenses or other miscellaneous deductions,
Have total itemized deductions that are more than the standard deduction to which you otherwise are entitled.