Here’s what HIVE AI had to say about “What kinds of expenses make itemizing worthwhile compared with the 2025 standard deduction levels?”:
To make itemizing worthwhile for 2025, your allowable Schedule A total generally needs to exceed your 2025 standard deduction amount: $15,750 (single or MFS), $23,625 (head of household), or $31,500 (MFJ or qualifying surviving spouse). 4
Expenses that most often drive itemizing above the 2025 standard deduction
- State and local taxes (SALT): state and local income (or sales) taxes plus real estate and personal property taxes, subject to the SALT cap; for 2025 the cap is $40,000 ($20,000 if MFS), with a reduction at higher MAGI levels. 5
- Home mortgage interest (and related home-interest items that are permitted on Schedule A, depending on your facts).
- Charitable contributions (gifts to qualified charities).
- Unreimbursed medical and dental expenses, but only the portion exceeding 7.5% of AGI. 6 1
- Personal casualty and theft losses from a federally declared disaster (subject to the applicable Schedule A rules/limits). 6
Expenses that commonly do not help (for most W-2 employees in 2025)
Many “miscellaneous itemized deductions” (for example, unreimbursed employee business expenses) generally aren’t deductible for tax years beginning after December 31, 2017 and before January 1, 2026 (i.e., through 2025), although certain items may still be deductible “above the line” as adjustments to income depending on the taxpayer’s status (for example, certain reservists and a few other categories). 2 3
Sources
1 – IRS – Publication 4696 VITA/TCE Puerto Rico Resource Guide 📄 Summarize
2 – Notice 2025-5 📄 Summarize
3 – IRS – Publication 529 Miscellaneous Deductions 📄 Summarize
4 – Credits and deductions for individuals
5 – How to update withholding to account for tax law changes for 2025
6 – It’s important for taxpayers to know the difference between standard
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