How do I figure out whether itemizing will beat the standard deduction for me?

Add up your deductible expenses for the year: state and local taxes (capped by the IRS), mortgage interest, charitable donations, and medical costs above the AGI floor. If that total is larger than the standard deduction for your filing status, itemize; if not, take the standard deduction. Because the standard deduction has been relatively high in recent years, the large majority of filers do better taking it, according to IRS data. Homeowners with a mortgage and generous donors are the most common itemizers. Keep receipts and year-end statements so you can run the comparison honestly. The Tax Strategies tool at wealthserene.com/tools/tax-strategies can help you tally deductions and see which path lowers your bill.