Choosing when to itemize deductions vs. the standard deduction comes down to one comparison: add up your deductible expenses for the year, and if the total is larger than the standard deduction for your filing status, itemize. If it isn’t, take the standard deduction. For the 2026 tax year, the standard deduction is $16,100 for single filers, $32,200 for married couples filing jointly, and $24,150 for heads of household.1Internal Revenue Service. IRS Releases Tax Inflation Adjustments for Tax Year 2026 Your combined mortgage interest, state and local taxes, charitable gifts, and other eligible costs need to exceed those numbers before itemizing pays off.
The Standard Deduction Is a Higher Bar If You’re 65 or Blind
If you are 65 or older or blind, an extra standard deduction stacks on top of the base amount. For 2026, that additional amount is $2,050 per qualifying condition for single filers and heads of household, and $1,650 per qualifying condition for married filers. A married couple where both spouses are 65 or older adds $3,300 to their $32,200 base, bringing their total standard deduction to $35,500. The higher the bar, the harder itemizing is to justify.
What Counts Toward Your Itemized Total
Itemized deductions are claimed on Schedule A.2Internal Revenue Service. About Schedule A (Form 1040), Itemized Deductions Tally each category below, then add the categories together to get the number that competes with your standard deduction.
State and Local Taxes (SALT)
State and local income taxes (or general sales taxes, if you choose that alternative), combined with property taxes, are deductible up to a $40,000 cap for most filers, or $20,000 for married filing separately.3Internal Revenue Service. Topic No. 503, Deductible Taxes The cap was raised from $10,000 starting in 2025.4Internal Revenue Service. How to Update Withholding to Account for Tax Law Changes for 2025 If your modified adjusted gross income exceeds $500,000 ($250,000 if married filing separately), the $40,000 cap phases down, but not below $10,000.
Mortgage Interest
You can deduct interest on up to $750,000 of mortgage debt ($375,000 if married filing separately) used to buy, build, or substantially improve your primary or secondary home. For mortgages that originated before December 16, 2017, the older $1 million limit ($500,000 if married filing separately) still applies. Interest on a home equity loan or line of credit is deductible only when the money was used to buy, build, or substantially improve the home securing the loan.5Internal Revenue Service. Publication 936 (2025), Home Mortgage Interest Deduction Home equity borrowing used to pay off credit cards or fund a trip doesn’t qualify.
Charitable Contributions
Gifts to qualified nonprofits count, whether in cash or property. Cash contributions to public charities are deductible up to 50% of your AGI, with lower limits for certain organizations and property gifts.6Internal Revenue Service. Charitable Contribution Deductions Property is valued at fair market value, and non-cash donations above $5,000 require a qualified written appraisal.7Internal Revenue Service. Publication 526, Charitable Contributions Amounts above the AGI limit can be carried forward up to five years.
Medical and Dental Expenses
Only the portion of unreimbursed medical and dental costs that exceeds 7.5% of your AGI counts.8Internal Revenue Service. Publication 502 (2025), Medical and Dental Expenses At $80,000 of AGI, the first $6,000 of spending doesn’t help; only dollars above that add to your Schedule A total. Qualifying costs include payments to doctors, dentists, and surgeons, prescription drugs, medical equipment, and health insurance premiums you pay out of pocket.
Casualty and Theft Losses
Personal casualty and theft losses are deductible only when tied to a federally declared disaster.9Internal Revenue Service. Publication 547 (2025), Casualties, Disasters, and Thefts A routine break-in or car accident outside a declared disaster area does not qualify. Even when a loss does qualify, it’s reduced by $100 per event and by 10% of your AGI.
Investment Interest and Gambling Losses
Interest paid on money borrowed to buy taxable investments is deductible, but only up to your net investment income for the year; the excess carries forward.10Office of the Law Revision Counsel. 26 U.S. Code 163 – Interest Gambling losses are deductible only up to the amount of gambling winnings you report as income, and only if you itemize. You cannot net wins against losses; you need a contemporaneous log of dates, wagers, locations, and amounts.11Internal Revenue Service. Topic No. 419, Gambling Income and Losses
Who Actually Comes Out Ahead by Itemizing
With the standard deduction where it is, most filers don’t clear it. The taxpayers who tend to benefit from itemizing share a common profile: a mortgage large enough to generate significant annual interest, property and state income tax bills that push toward or past the $40,000 SALT cap, substantial charitable giving, or an unusually heavy year of qualifying medical costs. If none of those apply, the math almost always favors the standard deduction, and no amount of tracking receipts will change that.
A useful sanity check: if your mortgage interest plus your capped SALT total is already close to your standard deduction, then modest charitable giving or medical spending can tip you into itemizing territory. If those two big-ticket items add up to a fraction of your standard deduction, the other categories rarely close the gap.
The Married Filing Separately Rule
If you and your spouse file separately, you must use the same deduction method. When one spouse itemizes, the other cannot claim the standard deduction and is forced to itemize too.12Internal Revenue Service. Tax Basics: Understanding the Difference Between Standard and Itemized Deductions That can hurt if one spouse has large deductible expenses and the other has almost none, because the second spouse ends up with an itemized total well below what the standard deduction would have given them. Before choosing separate returns, run the numbers both ways.
Running the Comparison and Keeping Records
Tax software handles the comparison automatically once you enter your expenses, defaulting to whichever number is larger. If you prepare your return by hand, put your Schedule A total next to the standard deduction for your filing status and use the higher one.
To back up an itemized return, you need documentation for each category. Form 1098 from your lender shows mortgage interest and deductible points.5Internal Revenue Service. Publication 936 (2025), Home Mortgage Interest Deduction8Internal Revenue Service. Publication 502 (2025), Medical and Dental Expenses13Internal Revenue Service. Charitable Contributions: Written Acknowledgments7Internal Revenue Service. Publication 526, Charitable Contributions Keep everything for at least three years from your filing date.14Internal Revenue Service. How Long Should I Keep Records?