Itemizing your Taxes Made Easier
This article has been updated for the 2022 & 2023 tax years. 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 take a look at 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.
Passing on the Standard Tax Deduction
Pre tax-reform, I was one of the 35-40% of Americans who itemized my taxes and did not take the standard deduction, and it paid off. I used to get excited about being able to itemize my taxes as I could see my tax obligation shrink with each added deduction or credit.
With the Tax Cut & Jobs Act (tax reform that went into effect starting in 2018), the standard deduction levels were doubled, and it’s now estimated than only about 10% of tax filers itemize their deductions now. The standard deduction levels are annually adjusted and indexed to inflation. The current standard deduction levels are:
2022 Standard Deductions:
- $12,950 for single filers
- $12,950 for married, filing separately
- $25,900 for married filing jointly
- $19,400 for head of household
- $0 personal exemption
2023 Standard Deductions:
- $13,850 for single filers
- $13,850 for married, filing separately
- $27,700 for married filing jointly
- $20,800 for head of household
- $0 personal exemption
This is quite a dramatic change over what the 2017 (pre-tax reform) 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.
Update: in 2021 there was a universal new charitable donation deduction for those that claimed the standard deduction. The 2021 charitable donation tax deduction for non-itemizers was $600 for “married filing jointly” and $300 for other filers. The universal donation deduction expired and is no longer active for 2022 or 2023.
3. Real Estate Expense Deductions
The State and Local Tax (SALT) deduction is the biggest itemized deduction for most people, often due to property tax amounts, but it was limited to $10,000 per year by tax reform. 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 form 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 7.5% of your gross AGI. 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 7.5% 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, aka the “Saver’s 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 (which come with significant affiliate partner discounts at the links):
- H&R Block
- Cash App Taxes (formerly “Credit Karma Tax”, now owned by Square/Cash App)
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?
Does itemizing make sense if you don’t own a home or didn’t make a major purchase in that tax year? I feel like it’s extremely difficult to get over the $5,700 standard deduction amount (and therefore, make it worth it to itemize) when I can’t deduct property tax, mortgage interest or sales tax on a major purchase. Thoughts?
@ Holykemp – it’s hard to answer that question b/c everyone has a slightly different situation. However, it’s much less likely that you’ll be able to deduct over the standard amount if you don’t pay mortgage interest and property tax. It’s still worth looking into, in my opinion, if you don’t own a home.
I haven’t itemized my deductions, but it certainly seems the way to go for homeowners and others who can deduct quite a bit from their return.
Even if you don’t pay mortgage interest or property tax, itemizing is much more likely to make sense if you tithe. 10% of your income can be a very large chunk of change, especially if that’s a pre-tax percentage…
If memory serves (this was *just discussed* in comments here, I think on the HAPPY post, and I looked it up later and verified — again, if memory serves) the medical expense deduction is only for the extent that medical expenses exceed 7.5%, not 0 for =7.5%.
Gah, angle brackets ate that last bit up — should have been:
not 0 for less than 7.5% and something much more than 0 if greater/equal to 7.5% (in other words, if you spend x% on medical expenses where x is more than 7.5, you can deduct (x – 7.5)% in medical expenses).
UPDATE: Thought I’d share an update and answer my own question. I did my taxes over the weekend and it did make sense for me to itemize, even though I don’t own a home and didn’t make a large purchase in 2009. BUT I do live in a state with a hefty 10% income tax. The tax paid for 2009 was higher than the standard deduction, so I’m itemizing to deduct the state income tax. I think that may have been what Jeff @ 5:51am was referring to?
No, tithing as giving money to your church; the historical meaning of tithing as an amount is at least 10% of your income, although there’s some disagreement over whether that’s pre-tax or post-tax. If you think it should be pre-tax, then making $57000+ in 2009 (not a particularly large salary in skilled fields, especially if you live somewhere where cost of living makes salaries higher) would alone make itemization worthwhile. The salary would have to be higher if you think the tithe is post-tax, but again depending on your field the necessary salary is still not unusually large.
Definitely a good thing. Donate now and get your money back within a few months when you file your tax return. I don’t itemize but I still donated to the Haiti relief.
My husband and I both work on the road for all of our jobs. My husband is a Boilermaker and I do Processing, although we are not self employed and do work for companys, we do not work from our home ever as it is 75 miles each way from the nearest nuclear plant and that bis where the majority of our work is. My husband is Union and pays Union dues, I am not. Is it better for us to itemize or is there a standard deduction for every day we are away from home, obviously, we stay out of town or out of state with when working, sometimes not seeing our home for months at a time. If itemizing is the way to go, how much of our actual expenses are we allowed to deduct? Thank you for any and all assistance/answers to this.
P.S. We usually pay a CPA to do this for us, to the cost of $650.00, so I thought this year I would try it myself!
Thanks again, Michele
Hey. I can’t help you much with your question but wondering if you know if they can write off field dues too. My husband is a boilermaker and pays union dues but then also has field dues come out of every paycheck…. Can we write that off as well or just the standard monthly dues ?
Union dues are deductible including the supplemental dues, in my case an average of 5,000. a year. If you have a good accountant, not H&R Block, I strongly recommend to use his/her services. It’s tax deductible and a good investment, talk to your friends about their Accountants, we are always willing to recommend excellent services. Good luck.
Since we bought a home this year I’m looking into itemizing for the first time. I have a few questions that I’m hoping someone may have insight on!
1) I know you can deduct points paid to lower the mortgage interest rate, but do those show up on a 1098 or any other form from the bank? Or do I just need to keep a copy of our lending agreement handy in case the IRS comes calling?
2) You CANNOT deduct regular commuting expenses (gas, car depreciation), right?
3) I live in a state with sales tax, but no income tax. Thoughts on adding up actual expenses vs. using the tax tables? If the tax tables are typically close I’d rather not take the time to add up all of my individual expenses.
Just answered question #1 for myself – my bank already has the 1098 statement ready, and “points paid” is a box on there.
When itemizing eligible expenses, would bank statements be enough documentation or is an actual receipt required?
I file the long form; Question. First time I have won at the Casino. Amount was $6200. I have been told I can claim or Submit Casino losses.which are documented through a players card annually from the casino. Also. i have kept $2500. in State Scratch Off losing tickets I have purchased in 2014., are these deductible items to add to my loss column? Thank You R Morris
Do you have a spreadsheet or something similar to list your deductions?
My wife passed away this year, I donated all her stuff to goodwill. 15 trips with a loaded SUV. The value was easily over $10,000 if not $15,000. I have mortgage interest and real estate taxes that last year did not exceed the standard deduction for a married couple. I do not have an appraised value. What is needed to get the full deduction?