3 Ways to Maximize Itemized Tax Deductions

Bundle Expenses To Maximize Itemized Tax Deductions

Woman calculating taxes owed.
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There are two types of deductions, standard or itemized. You should choose the one that lowers your taxes the most. Two out of three people claim the standard one because they don't have enough deductions to itemize—or because they aren't aware of how itemized deductions work.

Based on the new tax laws passed by Congress in 2018, more people qualify for the standard deduction than in the past but many will still pour over their receipts like in years past.

Here are the three ways you can potentially increase your itemized deductions.

1. Bundle Medical Expenses to Maximize Itemized Tax Deductions

When you incur medical expenses that are not covered by health insurance, you are only allowed to deduct them from your taxable income to the extent that they exceed 7.5% of your adjusted gross income.


Let’s say you are age 60 and make $50,000 a year. 7.5% of $50,000 is $3,750. If you have out-of-pocket medical expenses of $4,000, only $250; the amount that exceeds $3,750, would be eligible as an itemized tax deduction.

To maximize the use of this tax deduction, you need to do 3 things:

  1. Each year calculate an estimate 7.5% of your adjusted gross income.
  2. Keep a running total of your out-of-pocket medical expenses each year.
  3. If you have a year where you are nearing your threshold, determine if there are expenses you can bundle into the current calendar year.

2. Pre-Pay State Taxes 

State income taxes paid are an itemized tax deduction on your federal return. Many people can benefit by paying their state income taxes before year end in order to maximize their deductions for federal taxes.

Be careful, as this strategy can possibly throw you into AMT (alternative minimum tax), although this issue not of as much concern anymore since the Tax Cuts and Jobs Act (TCJA) significantly reduced the impact of AMT for most taxpayers. However, tax reform did throw some different wrenches into pre-paying state taxes. Be careful, as this strategy won't work for everyone. Remember, the Tax Cuts and Jobs Act of 2017 capped the deduction for state and local taxes at $10,000. So if prepaying your state income taxes will push you over this limit, you might not benefit from making your payment early. Also, the law prohibits pre-payments for income tax to be used as a deduction in the current year. In other words, you can pay what you expect to owe the state for your 2020 tax return before December 31, 2020 and claim a deduction on your 2020 tax return. However, if you try paying your 2021 taxes in 2020, the IRS will treat the payment as if it had been paid in 2021. If you plan on prepaying a substantial amount of state tax, consult with a tax advisor to make sure this strategy will work for you.

If you plan on prepaying a substantial amount of state tax, consult with a tax advisor to make sure this strategy will work for you.

3. Casualty Losses

There were over 120 federal national disasters declared in 2018. With that declaration, anybody affected is eligible for a casualty loss deduction for losses incurred as a result of those disasters. The loss must exceed $100 and can be deducted only to the extent that they exceed 10% of adjusted gross income.

For the many Americans that suffered loss due to fires, flooding, and other disasters this deduction could be a welcome relief.

Be sure to check to see which tax deductions have expired and which ones have been extended for the tax year that you're filing for—you may be able to qualify for more than you realize.

Many Itemized Deductions Gone

In the past you could deduct investment fees, tax prep fees, and a slate of theft and casualty losses that didn't require a disaster declaration. When the new tax laws went into effect in 2018, those deductions went away. Although the standard deduction is now higher, the slate of allowable deductions contracted.

If you haven't itemized your deductions in the past, don't rely on old knowledge. Ask for help from a tax professional to avoid costly mistakes.