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Have you ever wondered whether you’re better off itemizing your tax deductions or simply taking the standard deduction? How much more difficult is it to itemize? Would you get a bigger tax break? And, well, what is itemizing anyway? We have the answers.

Let’s take a look at some of the most common itemized deductions, whether you’re eligible to deduct them, and if it would save you money come tax time.

Standard Deduction vs. Itemizing

If you’ve ever done your taxes, you’re likely aware that all taxpayers (companies and individuals) are allowed to deduct certain expenses from their tax bill each year. The purpose of this is to lower everyone’s overall tax burden and ensure that at least some of each taxpayer’s earnings are not subject to federal income tax.

Standard Deduction

For simplicity’s sake, and to level the playing field, the IRS has instituted a flat (or standard) deduction that anyone can take. The standard deduction dollar amount is based on your filing status: single, head of household, married filing jointly, or married filing separately.

For the 2019 tax year, this amount ranges from $12,200 to $24,400. There is an additional provision of between $1,300 and $1,650 for those over 65 or legally blind.

2019 Filing StatusStandard Deduction
Single$12,200
Head of Household$18,350
Married Filing Jointly$24,400
Married Filing Separately$12,200
Qualifying Widow(er)$24,400
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There are a few instances when you wouldn’t be able to take the standard deduction:

  • If you file married filing separately, and your spouse itemizes deductions on his or her return
  • If you’re filing jointly and you (or your spouse) were a non-resident alien at any point in the tax year
  • If you alter your accounting period and end up filing a return that covers a period shorter than 12 months

Itemizing Deductions

So, what exactly does it mean to “itemize your deductions?”

As the name suggests, deciding on itemized deductions means that you choose to calculate, one-by-one, all the tax-deductible expenses on your tax return, rather than opting for the flat deduction.

This is beneficial if your eligible deductions add up to more than the standard deduction. You want to pick whichever one results in a higher number so you get a bigger tax break in the end.

Recent Tax Changes

Beginning with the 2018 tax year, the IRS made some serious changes that affected pretty much every tax filer in the United States.

This recent tax reform included an overhaul of many things but for many filers, the most impactful was the increase in the standard deduction.

For tax year 2017, the standard deduction for a single filer was a mere $6,350. For tax year 2018, this nearly doubled to $12,000. All other filing categories saw a huge bump in the standard deduction as well, much to the surprise (and joy) of filers everywhere.

However, this boost created some new questions, mostly when it comes to itemizing versus taking the standard deduction.

Does It Still Make Sense to Itemize?

The IRS hasn’t yet published the final tax filing numbers from last April, which covered tax year 2018. However, it was projected that only about 13% of filers would bother itemizing under the new tax law, simply because it wasn’t the best move financially.

Itemizing only makes sense if you stand to deduct more from your taxes than you would by taking the standard deduction. Yes, the itemized deduction route is more work (another reason many taxpayers will automatically opt for that route) but you should consider itemizing if any of the following apply to you in the last tax year:

  • You made large charitable donations.
  • You own a home and paid home mortgage interest.
  • You have expenses related to investment income.
  • You (or your dependents) have medical expenses beyond the occasional doctor’s visit.
  • You paid property, state, or local income taxes.
  • You have miscellaneous deductions to include.

Itemizing your deductible expenses is definitely more of a hassle than taking the standard deduction. It’s well worth it, though, if it will reduce your tax burden.

If you think there’s a chance that your deductible expenses are greater than your personal standard deduction amount, take time to run the numbers. Many online tax preparation companies will even help you with this and offer a suggestion on whether you should itemize or not.

Related: File your federal taxes for FREE with Turbo Tax

Common Itemized Deductions

1. Charitable Donations

Were you generous last tax year? Did you tithe to your church, contribute to a worthy cause, or donate your gently used household items to those in need? If so, you can probably claim these gifts as itemized deductions.

There are a few limitations to charitable deductions. First and foremost, you must donate to a qualified organization. Political campaigns don’t count, and you’ll need to get a receipt to support your contribution claim.

There are also dollar amount limits. For cash donations, you can only claim a deduction up to 50% of your AGI. For certain private foundations, veterans’ organizations, nonprofit cemeteries, and fraternal societies, this limit is even lower at 30%. You’re also limited to a 30% AGI deduction for personal property donations.

In order to donate property (such as household goods, clothing, etc.), it needs to be in good, usable condition. You also have to determine the fair market value — you can’t just claim the new value for non-cash donations. If you need help determining the donated item’s value, check out this guide.

2. Home Mortgage Interest

If you have a home (or two), you’re eligible to deduct the interest paid on that mortgage as an itemized deduction. Depending on where you are on your mortgage term, this is likely a substantial amount, too.

The mortgage interest deduction is allowed on the first $750,000 of the mortgage. Each taxpayer is allowed to deduct interest paid on as many as two residences, as well.

While you used to be able to deduct the interest paid on a home equity loan, this is no longer the case.

3. Investment Expenses

Investing often brings with it a slew of expenses, including legal and professional fees, financial advice, and more. Luckily, many of the expenses involved with these “income-producing activities” are tax-deductible, if you itemize.

You can deduct your investment expenses on the Schedule A as long as they don’t exceed your investment income for the year. Essentially, you can’t report a loss on your itemized deductions based on investment expenses alone. (Claiming a capital loss on the investment value itself is a different matter, though.)

You can deduct expenses such as:

  • Fees paid to a bank, trustee, or broker
  • Fees paid to collect your investment income, or your dividends on stock shares
  • Fees paid to a lawyer, accountant, or clerical help that is necessary to produce taxable income
  • Fees paid to a financial/investment advisor
  • Monthly bank fees paid in order to enroll in auto-investment services
  • Safe deposit box expenses in order to store investment-related documents
  • Investment-related publications to which you subscribe
  • Office expenses that are strictly used for managing investments and earning income from them
  • Online services or software used to manage your investments

You can not deduct expenses like:

  • Investment fees on publicly-traded mutual funds, as these are already deducted from your share and aren’t explicitly paid
  • Expenses involved with attending investment seminars, conventions, or meetings (sorry–that trip to the annual Berkshire Hathaway shareholder meeting isn’t going to count!)
  • Expenses involved in producing tax-exempt income
  • Broker fees paid to acquire investment property (stocks, bonds, etc)*
  • Any state or local transfer taxes incurred when you buy/sell securities*

*instead, expenses on both of these are added to the cost of the property

Related: File your federal taxes for FREE with H&R Block

4. Medical Expenses

These are a bit trickier, from a tax-deductible standpoint, but you can claim medical expenses on your itemized deduction.

The caveat is that you can only claim that which exceeds 7.5% of your AGI. This means that if you make $60,000 a year, you can only claim eligible expenses over and above the first $6,000.

If you reach your 7.5% AGI limit, there is a long range of expenses that you can deduct. These include:

  • Co-pays and doctor’s fees, even if you saw a chiropractor or non-traditional provider
  • Insurance premiums
  • Medically-necessary surgery costs (no, cosmetic surgery doesn’t count, unless it was reconstructive)
  • Prescriptions
  • Expenses related to attending a medical conference for a chronic condition that you, your spouse, or a dependent have (limited to transportation and admission)
  • Contact lenses, glasses, or hearing aids
  • Crutches, wheelchairs, guide dogs, or other accessibility expenses
  • Dental work
  • Weight loss programs for those with diagnosed obesity (but special food isn’t necessarily included)
  • Alcohol, drug addiction, and nicotine cessation treatment
  • Transportation involved with receiving medical care (fares, tolls, parking, and gas/oil)

5. Local, State, and Property Taxes

If you live in a state with its own income taxes, you’ll likely benefit from itemizing. Local (city) or state taxes incurred during the year are deductible on the Schedule A.

You can also deduct any real estate taxes that you paid on your home, as well as personal property taxes that you paid on belongings like your vehicle (a lovely, added expense we have here in Virginia).

You cannot deduct federal income tax, estate taxes, Social Security taxes, homeowner’s association fees, or transfer taxes from the sale of a home, among others.

6. Miscellaneous Expenses

There are a few tax-deductible expenses that don’t fall into any of the above categories, but you can still claim them when you itemize your deductions. They are limited to expenses above 2% of your AGI. Using the example above, where you make $60,000 a year, this means that you would only be able to deduct expenses above $1,200.

These include things like:

  • Tax-preparation fees from the year prior
  • Home office expenses
  • Legal fees
  • Job-hunting and interviewing expenses
  • Work-related expenses that weren’t already reimbursed
  • Subscriptions to professional journals, etc.
  • Licensing and regulatory fees
  • Union dues
  • Uniforms

Depending on how much you make each year and which additional expenses you incur, itemizing your deductions (rather than taking the standard deduction) might be a wise idea. It’s important to do the math (most tax-preparation software can analyze this for you) and see which is the most financially-beneficial option.

As with everything tax-related, you’ll need to keep diligent records and save receipts for everything that you believe to be a deductible expense.

Consult a Tax Pro

The editorial team at Dough Roller knows a thing or two about taxes. Some have taken the standard deduction, others have itemized. We’ve prepared our taxes with software like TurboTax, and we’ve also hired pros.

But we are not tax experts. We’ve done our best to get the above information right and offer clear guidance, but please consult a tax professional before making any decisions.

Author Bio

Total Articles: 100
Stephanie Colestock is a respected financial writer based in Washington, DC. Her work can be found on sites such as Investopedia, Credit Karma, Quicken, The Balance, Motley Fool, and more, covering a range of topics such as family finances, planning for the future, optimizing credit, and getting out of debt. She is currently working toward her CFP certification. Her full portfolio can be found at stephaniecolestock.com.

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