Should I Itemize With the New OBBBA Changes?
If you’ve taken the standard deduction for years, you’re not alone. But with recent tax law changes under the One Big Beautiful Bill Act (OBBBA), more people - especially higher-income taxpayers - are starting to ask: how do I know if I should itemize deductions? For many of Ken-Mar Tax’s clients, the answer is changing. And in some cases, itemizing now makes more sense than it did in the past.
What Changed Under the OBBBA?
The OBBBA made some permanent changes that impact how deductions work. One of the biggest shifts is that certain write-offs, like unreimbursed employee expenses, are no longer allowed at all. But that doesn’t mean itemizing is off the table. In fact, several major deductions are still available, including mortgage interest, state and local taxes, charitable contributions, and medical expenses. For the right taxpayer, those can add up quickly.
Why More People Are Starting to Itemize Again
In the past, the standard deduction was often the easier and better option. But now, depending on your income and expenses, itemizing can produce a larger tax benefit. This is especially true if you:
- Own a home with significant mortgage interest
- Pay higher state or local taxes
- Make consistent charitable contributions
- Have higher medical expenses in a given year
For many higher-income individuals, these categories alone can push total deductions beyond the standard amount.
When Itemizing May NOT Make Sense
Even with the changes, itemizing isn’t always the better move. If your total deductions don’t exceed the standard deduction, you won’t benefit from itemizing. And for some taxpayers in the highest income bracket, the value of itemized deductions may be reduced under the new rules.
Starting in 2026, taxpayers in the top tax bracket may see their itemized deductions limited, which can reduce the overall benefit. This is where things become less obvious and more dependent on your specific situation.
Why This Isn’t a Simple Yes or No Decision
On paper, the rule is simple: take whichever deduction is higher - standard or itemized. But in reality, it’s not always that straightforward. Timing, income levels, and how deductions are structured can all affect the outcome. For example, bunching charitable contributions into one year or managing income levels strategically can change whether itemizing makes sense.
This is where planning - not just filing - makes the difference.
How This Affects Higher-Income Taxpayers
For clients with higher income, this conversation becomes even more important. Some taxpayers who never itemized before are now seeing real benefits from doing so. Others need to be more strategic to avoid losing value from their deductions. The key is understanding where you fall and how the rules apply to you.
The Bottom Line: Should You Itemize?
It depends - and the answer may be different than it was a few years ago. With the changes under the OBBBA, more taxpayers are finding that itemizing deductions is worth revisiting. But it’s not something you want to guess on or assume based on past years.
Not Sure What Makes Sense for You? Let’s Take a Look
If you’re not sure whether you should itemize or take the standard deduction, it’s worth reviewing your situation before filing. A small change here can have a noticeable impact on what you owe. When you work with Ken-Mar Tax, you’re not just getting a return prepared - you’re getting a strategy behind it. And if questions ever come up, you have someone who can represent you with the IRS, Ohio, and RITA.
Reach out when you’re ready. We’ll take a look and make sure you’re making the right decision for your situation.
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Small Business Tax Services
As an expert in small business tax services and tax consulting Ken-Mar Tax eats, sleeps and breathes small business tax strategies. Being an enrolled agent allows founder, Ken Weinberg, to represent you to the IRS - something only a CPA, tax attorney and Enrolled Agent can do. EAs are the only federally licensed tax practitioners who specialize in taxation and also have unlimited rights to represent taxpayers before the IRS. It also means he is continuously being updated on the new IRS tax codes and taking classes from the IRS that provide guidance on how to file returns so that they are not "flagged."
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