You take one or the other, never both
Every taxpayer subtracts a deduction from AGI to arrive at taxable income, and you choose the bigger of two options: the flat standard deduction, or the total of your itemized deductions. For 2026 the standard deduction is $16,100 single, $32,200 married filing jointly and $24,150 head of household. It requires no receipts and no substantiation, which is why roughly 90% of filers take it.
If you are 65 or older two separate additions apply. The long-standing one adds $2,050 (unmarried) or $1,650 per qualifying spouse (married), with the same amounts again for blindness. On top of that, the OBBBA senior deduction adds up to $6,000 per qualifying filer, phasing out above $75,000 of income ($150,000 married). A retired couple both over 65 therefore weighs their itemized total against $35,500 ($32,200 plus $1,650 each), not $32,200. The $6,000 senior deduction each is taken whether they itemize or not, so it does not change that comparison, but the extra $3,300 is easily enough to flip the answer, which is why the calculator asks.
What counts as an itemized deduction
- State and local taxes (SALT): income or sales tax plus property tax, capped at $40,400 for 2026 ($20,200 married filing separately). Above $505,000 of income that cap phases down by 30¢ per dollar, never falling below $10,000. For many homeowners this is the largest single item.
- Mortgage interest: on acquisition debt within the applicable limits, reported on Form 1098.
- Charitable contributions: cash and property to qualified organizations, with written acknowledgement required for gifts of $250 or more. New for 2026: only the amount above 0.5% of your AGI counts, so at $100,000 of AGI the first $500 of giving is not deductible.
- Medical and dental expenses, but only the portion above 7.5% of your AGI. At $100,000 of AGI the first $7,500 of medical costs counts for nothing.
- Casualty losses in federally declared disaster areas.
Notably absent since 2018: unreimbursed employee expenses, tax preparation fees, and investment fees.
The break-even test
Itemizing only helps to the extent your total exceeds the standard deduction. If a married couple has $30,000 of itemized deductions against a $32,200 standard deduction, itemizing would cost them $2,200 of deduction. The standard deduction wins. And the benefit is only the difference: $35,000 itemized against $32,200 standard is a $2,800 advantage, worth about $616 in the 22% bracket, not $35,000 of savings.
Taking the standard deduction no longer costs you the charity write-off
Also new for 2026: if you take the standard deduction you can still deduct up to $1,000 of cash gifts ($2,000 married filing jointly) on top of it. That is a genuine change in the break-even math. For the first time since 2021, ordinary donors get a tax benefit without itemizing. The comparison above counts it on the standard-deduction side, which is why the standard route can total more than the headline amount.
Bunching: the strategy that changes the answer
If you're close to the line every year and never quite clear it, consider bunching: compress two years of deductible spending into one. Make January's charitable gift in December alongside the current year's, prepay a property tax installment, or schedule elective medical work into a single year. You itemize in the heavy year and take the standard deduction in the light year, capturing more total deduction across the two than you would by splitting them evenly. A donor-advised fund makes this straightforward for charitable giving. You deduct the lump contribution now and distribute the grants over following years.
Then check what it's actually worth
Whichever you take, the deduction reduces taxable income, not tax. Its value is the amount multiplied by your marginal rate. Feed the result into the taxable income calculator to see your final figure, and read our standard vs itemizing guide for the full break-even math. Note that married couples filing separately must both make the same choice.