Thinking of Itemizing your Tax Deductions? Here’s a Teaser

Itemizing your Taxes Made Easier

If you’re like me, you’re probably still waiting around for all your income statements to trickle in from banks, discount brokers, your employer, and anyone else whom you might have some sort of financial interest with.




The part that is more in your control is the organization of your deductions. If you’re not sure whether or not itemizing your taxes is right for you, you may want to visit IRS Form 1040. What follows will be a teaser on what you could potentially itemize and how to organize your tax deductible expenses throughout the year.

itemizing taxes

Passing on the Standard Tax Deduction

I’m one of those 35-40% of Americans who doesn’t take the standard deduction, and it has paid off. I get excited about being able to itemize my taxes. However, in doing so, I’m quickly finding that with each passing year, preparing for my tax return keeps getting progressively difficult.

With the Tax Cut & Jobs Act (tax reform), the standard deductions have been increased, and I would expect that significantly fewer taxpayers will be itemizing their deductions moving forward:

2019 Standard Deductions:

  • $12,200 for single filers
  • $12,200 for married, filing separately
  • $24,400 for married filing jointly
  • $18,350 for head of household
  • $0 personal exemption

2020 Standard Deductions:




  • $12,400 for single filers
  • $12,400 for married, filing separately
  • $24,800 for married filing jointly
  • $18,650 for head of household
  • $0 personal exemption

This is quite a dramatic change over what the 2017 standard deductions were:

  • $6,350 for single filers
  • $6,350 for married, filing separately
  • $12,700 for married filing jointly
  • $9,350 for head of household
  • $1,050 for dependents
  • $4,050 personal exemption

A List of Tax Deductions by Category

Itemizing your taxes can be fairly straightforward – but much more so if you prepare year round. I have a simple way of dealing with tax documents in lieu of itemizing that has worked for me over the years. I’d recommend grabbing some manila folders and labeling them. Here’s how I group tax related paperwork for deductions:

1. Investment Loss Deductions

This includes capital loss deductions for losses from mutual funds, stocks, and other investments. If you get electronic statements from your online brokers, you may actually need to go into your account online and print off your 1099-B tax forms.

2. Charitable Donation Deductions

If you have record of a gift that you gave to a 501(c)(3), hold onto them. Also, you may be able to deduct mileage and other expenses from volunteering your time and efforts for a non-profit. Here’s complete documentation on IRS deductible charitable donations and my guide on donation receipts (I used to work at a non-profit). Note that there is a IRS maximum charitable donation limit, which is based off your income level and what type of organization you contribute to.

3. Real Estate Expense Deductions

If you own a home, you’ll need a copy of your tax bill or a statement from your escrow company on how much in property taxes you paid over the year. Those with mortgages will need a 1098 from their mortgage provider. Those lucky enough to claim the first-time homebuyer credit will need to attach IRS Form 5405. Also, don’t forget energy tax credits for things like wind and solar installations.

4. Education Expense Deductions

Education tax deductions and credits include tuition paid (IRS Form 1098-T), interest paid on student loans (IRS Form 1098-E), college expenses (books, travel, etc.).

5. Family Expense Deductions

Have a family? You probably need some deductions these days. Deductible expenses include child and dependent care expenses, adoption expenses, child tax credits, and earned income tax credits.

6. Personal Property & Vehicle Deductions

In this category you can lump in any vehicle registration fees, personal property taxes paid, and tax credits for electric vehicles (including potential state electric vehicle tax credits).

7. Medical & Dental Expense Deductions

You can deduct medical and dental expense that exceed 10% of your gross AGI (temporarily restored to 7.5%, as in prior years, with extender tax legislation). These expenses can include medical bills, prescriptions costs, medical equipment costs, insurance premiums, and miles driven for medical purpose. Payments to HSAs are also tax deductible if you itemize, regardless if you hit the 10% on other medical expenses.

8. Retirement & Investment Expense Deductions

Getting money back for investing is great! HSA, Traditional IRA, SIMPLE IRA, Solo 401K, & SEP IRA contributions are tax deductible. Your 401K, 457B, and 403B contributions should already be factored in through payroll and your W2. Also, if you’re under certain income thresholds, you may be able to claim the Retirement Savings Contribution Credit.

9. Employment Expense Deductions

You can no longer claim a deduction for unreimbursed employee expenses unless you fall into one of the following categories of employment, or have certain qualified educator expenses.

  • Armed Forces reservists.
  • Qualified performing artists.
  • Fee-basis state or local government officials.
  • Employees with impairment-related work expenses.

Unreimbursed employee expenses for individuals in these categories of employment are deducted as adjustments to gross income. Qualified employees listed in one of the categories above must complete Form 2106 to take the deduction. Certain qualified educator expenses are also deducted as an adjustment to gross income but you are not required to complete Form 2106.

You can deduct only unreimbursed employee expenses that are:

  • Paid or incurred during your tax year,
  • For carrying on your trade or business of being an employee, and
  • Ordinary and necessary.

10. Miscellaneous Deductions

If you have miscellaneous deductions that exceed 2% of your AGI, you can deduct them. This includes a wide variety of expenses that you might not think are deductible.

Update: the miscellaneous deduction was eliminated with the Tax Cuts & Jobs Act.

Itemizing Taxes Summary

Itemizing your tax deductions isn’t the easiest or most enjoyable thing in the world to do, but it can potentially pay huge dividends for you. If you’re looking for more tips, check out my guide on how to do your taxes.

If you pay your credit card balance in full (mandatory here), you can profit by paying your taxes with a credit card and even deduct the expense of the processing fee.

To help you figure this all out, check out my list of the cheapest and best tax software for more info, including feature comparisons. I’ve always used DIY tax software and it has helped me understand all the ins and outs of what deductions I can claim, what losses I can write off, etc. Here are my top 4 picks:

  1. H&R Block: 30% off at link!
  2. Turbotax: $20 off online versions at link!
  3. TaxAct: 30% off at link!
  4. Taxslayer: 50% off at link!

Reader Tax Deduction Discussion:

  • Are you itemizing your taxes this year?
  • Would you add any major buckets of deductions to this list?
  • How long have you been itemizing?
  • Do you get excited about itemizing your taxes?

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