How the Deduction Choice Works
After calculating your adjusted gross income (AGI), every taxpayer gets to subtract either the standard deduction or their total itemized deductions from that number — whichever is larger. The standard deduction is a flat dollar amount set by Congress and adjusted each year for inflation. For 2024, it is $14,600 for single filers, $21,900 for head of household, and $29,200 for married filing jointly.
Itemized deductions require you to list and document individual deductible expenses on Schedule A of your tax return. This takes more effort, but for some taxpayers the total exceeds the standard deduction, making it worthwhile. You are never required to itemize — the choice is always yours, and you should always choose whichever option produces the lower tax bill.
The decision comes down to simple math. Add up every expense you could deduct on Schedule A. If that total exceeds your standard deduction, itemizing saves you more. If not, take the standard deduction and move on. Tax software handles this comparison automatically, but understanding the mechanics helps you plan throughout the year.
What You Can Itemize
Itemized deductions on Schedule A cover several categories of expense. Mortgage interest is deductible on acquisition debt up to $750,000 under the Tax Cuts and Jobs Act (TCJA) of 2017. State and local taxes paid — a category called SALT — are deductible but capped at a combined $10,000 for income or sales taxes plus property taxes. This is the deduction most people mean when they talk about "writing off" their property taxes.
Charitable contributions to qualifying organizations are deductible, whether cash or non-cash property like donated clothing or stock. Unreimbursed medical and dental expenses are deductible only to the extent they exceed 7.5% of your AGI — so if your AGI is $80,000, only medical expenses above $6,000 are deductible. Casualty losses from federally declared disasters are also included, though this category has become quite narrow. Investment interest expense can be deducted up to the amount of your net investment income.
The phrase "writing something off" is often used loosely in everyday conversation. What it almost always means in practice is claiming an itemized deduction — reducing taxable income by the amount of a qualifying expense. It does not mean the expense is free; it means you recover a fraction of its cost through a lower tax bill, with the fraction determined by your marginal tax rate.
TCJA Changed Everything
Before the Tax Cuts and Jobs Act took effect in 2018, roughly 30% of American taxpayers itemized their deductions. TCJA made two changes that dramatically shifted this calculation. It roughly doubled the standard deduction, and it capped the SALT deduction at $10,000. The combination meant that many households who had previously itemized — primarily homeowners in high-tax states — no longer had enough deductible expenses to beat the new, higher standard deduction.
By 2024, fewer than 11% of taxpayers itemize. For most Americans, itemizing is no longer worth the effort. Mortgage interest deductibility — once the cornerstone of itemizing for middle-class homeowners — became far less valuable because the higher standard deduction often exceeds whatever itemized deductions a typical household can document.
The taxpayers who still benefit from itemizing tend to share a few characteristics: they own expensive homes with large mortgages, live in high-tax states, make substantial charitable contributions, or have significant out-of-pocket medical expenses. If none of those apply, the standard deduction is almost certainly your better option.
The Bunching Strategy
If your annual itemized deductions consistently land near but just below the standard deduction threshold, a strategy called bunching can help you capture more value from itemizing over time. The idea is to concentrate deductible expenses — especially charitable giving — into alternating years rather than spreading them evenly.
Instead of donating $8,000 to charity each year, you give $16,000 every other year. In the giving year, your itemized deductions may push past the standard deduction threshold, generating a larger deduction than you would have claimed otherwise. In the off year, you take the standard deduction. Over two years combined, you deduct more than you would have by taking the standard deduction each year.
Donor-Advised Funds make bunching practical and flexible. You contribute the full $16,000 to the fund in Year 1 and claim the deduction immediately. You then direct grants from the fund to your chosen charities at whatever pace you like — including over multiple years. The charities receive their support on a schedule that works for you, while you receive the tax benefit upfront in the bunching year.