10 Creative (But Legal) Tax Deductions

The 2017 Tax Cuts and Jobs Act essentially eliminated moving expenses for most federal income tax filers. But that only applies to tax years 2018 and beyond. If you are able to amend a past return from 2017 or earlier, you could still take the deduction for qualified moving expenses.

Also, active duty members of the U.S. Armed Forces can still deduct unreimbursed moving expenses from both domestic and foreign moves. See the Instructions for Form 3903 for more information. If you are able to amend a past income tax return from 2017 or earlier, note that the IRS applied two basic "tests" to determine if you could deduct moving expenses: distance and time. First, the distance test: If you moved for a new job — or even to find a new job — the new location must have been at least 50 miles (80 kilometers) farther than the distance of your old commute [source: IRS]. So if you used to drive 30 miles (48 kilometers) to work, the new location had to be at least 80 miles (129 kilometers) from your old home. If you're self-employed and work from home, then you only had to move 50 miles away, which can be as close as the neighboring city or town.

Now the time test: Once you moved into your new location, you must have been employed full time for at least 39 weeks of the next 12 months. What's great about this is that you didn't have to work for the same company that brought you out to the new location. Even if you quit that job or got canned, you could still deduct the moving expenses if you got another job in the same geographical area that kept you employed for the minimum 39 weeks. Note that if you were self-employed, the time rule is more strict; you must have remained employed full time for at least 78 weeks of the next 24 months after the move [source: IRS].

What exactly did the IRS let you deduct as moving expenses?

The cool thing about moving expense deductions was that they were an "above the line" deduction, meaning you didn't have to itemize deductions to claim them [source: Bischoff]. Now let's look at some ways to get creative with education expenses.

The U.S. tax code is designed to encourage certain purchases and activities that strengthen society. Home ownership is one of those, and so is higher education. That's why the Internal Revenue Service (IRS) lets you deduct the interest you pay on both home mortgage loans and student loans. But did you know that you can deduct the interest paid on student loans — even if you aren't the person that's paying it? If you qualify, you can deduct up to $2,500 in student loan interest every year.

As the IRS sees it, the person who is legally obligated to pay back a student loan has the right to deduct the interest. In most cases, that person is the student. So even if your parents are the ones writing the check each month, you can still deduct that interest on your tax return.

With the IRS being the IRS, nothing is straightforward, so there are a few conditions that could potentially disqualify you from claiming the interest deduction on your tax return:

Now let's look at some creative deductions you can take from contributing to a good cause.

If you donate money to your church or another tax-exempt organization, you are allowed to deduct those cash donations from your taxable income. The same is true for non-cash donations like used items donated to Goodwill. But did you also know that you can deduct expenses incurred from volunteer work or other charitable activities? Thanks again, IRS!

Let's say you mentor a kid across town as part of the Big Brothers, Big Sisters program. You drive 20 miles (32 kilometers) every week to meet him at his apartment. You buy reading and math workbooks to complete together. Every month, you take him to the museum or the zoo or a children's music concert. All of these out-of-pocket expenses support a volunteer activity with a tax-exempt charitable organization. So all of these expenses are deductible, including:

Don't let your charitable nature cheat you out of well-deserved tax deductions. If you really want to get creative, you can even deduct the expenses of the flour and sugar you buy to make cookies for the school or church bake sale fundraiser.

Next, we'll look at the creative (but dangerous) world of home office deductions.

Before we get too deep into this one, heed this warning: Home office deductions are a huge red flag for the Internal Revenue Service (IRS). The IRS has established a strict set of rules on home office deductions and too many taxpayers try to flaunt them. So unless you have a perverse love of audits, rein in your creativity on this one.

According to the IRS, a portion of following expenses may be deducted for a qualifying home office [source: IRS]:

Instead of itemizing, you can opt for taking a standard deduction of $5 per square foot of home office space, up to 300 square feet.

Again, the IRS is a stickler on this one. A qualifying home office is a part of the home that is used "exclusively and regularly" as the principal place of business [source: IRS]. Ideally, it's a separate structure from the living quarters of the house. If not, then it needs to be a place set aside exclusively for business purposes. People get into trouble when their bedroom doubles as their graphic design studio, or they work from home a couple of days a week because the commute is too long [source: Turbotax].

But if you already have a portion of your home set aside exclusively for business purposes, then you have the right to take as many deductions as you deserve. For example, if you regularly meet clients or customers in your home office, you can deduct the cost of repairs and maintenance — even landscaping — to the home that make it more presentable [source: TurboTax].

Note that if you temporarily worked from home for an employer during the COVID pandemic, you cannot deduct home office expenses. The IRS reserves home office expenses for self-employed workers and sole proprietors [source: TurboTax].

Now let's see how you can save tax dollars by turning your hobby into a small business.

You love growing vegetables. You love growing vegetables so much that you sell your extra produce at the local farmers market. But when you add up the money you invest each year in seeds and fertilizer and equipment repairs, you realize that this is becoming an expensive hobby. The problem is that the Internal Revenue Service (IRS) doesn't allow you to deduct expenses related to hobbies. Instead of scaling back your garden, however, why not turn your passion into a small business?

You don't have to jump through a bunch of legal hoops to start a small business. If you're a sole proprietor, you simply report your business income and expenses on Schedule C of your normal 1040 tax return. The perk is that you can deduct all of the "ordinary and necessary" expenses related to your business, even if you don't make a profit. Seeds, fertilizer and farmer's market signs are all ordinary and necessary expenses for a market gardener.

But here's where things get tricky. Whether or not your small business is profitable, the IRS insists that there be a "reasonable expectation of earning a profit" [source: Turbotax]. If you claim business losses year after year, the IRS might question whether this hobby-turned-business is really just a tax shelter. The best way to prove your legitimacy is to pass something called the "three of five" test [source: Nolo]. If your business was profitable in at least three out of the past five years, the IRS should leave you alone.

For the next creative deduction, we look at that morning commute.

First, the bad news: If you drive miles to work every day in gridlock traffic, and then suffer through the same living hell on the way back home, the IRS won't give you a dime for your troubles. For some strange reason, you can deduct all sorts of expenses when traveling for business, but not when traveling to and from your regular place of business. But now the good news: There's a loophole.

A growing number of employers in America are participating in commuter benefit programs like the one operated by TransitChek. If your employer enrolls with TransitChek, you can opt to make pretax deductions from your monthly paycheck to cover commuter expenses. Those include everything from parking costs to bus passes. Since the money is withheld from your paycheck before taxes, it functions as a deduction from total taxable income.

For tax year 2021 (2022), the maximum monthly deduction is $280 for qualified parking and transportation [source: Patriot Software].

For the next creative deduction, we'll look at unconventional medical expenses.

The IRS allows you to deduct medical expenses as itemized deductions, but only if the expenses are greater than 7.5 percent of your adjusted gross income [source: IRS]. Even if you consider yourself a relatively healthy person, you might want to read the fine print on Schedule A.

For starters, you can deduct medical expenses for yourself, your spouse and any dependents. Not only are you allowed to claim out-of-pocket expenses from doctor's office visits and medications, but also unconventional practitioners like chiropractors, acupuncturists, Christian Science practitioners, and pretty much anyone who can write a note saying that the treatment is medically necessary [source: IRS]. There are even taxpayers who have successfully deducted the expense of installing a backyard swimming pool because a doctor said it would help treat their emphysema [source: TurboTax].

And don't forget about travel expenses. You can deduct up to 16 cents a mile for driving back and forth from medical treatments, including meetings for programs like Alcoholics Anonymous [source: IRS]. You can even deduct the cost of traveling to a conference about your specific medical condition, although the costs of meals and lodging are on you.

If you have a child with a diagnosed learning disability, you can also deduct the cost of any special education programs and therapies, the mileage traveled to those therapies, and even the tuition costs for higher education programs specifically for people with learning disabilities [source: Wardwell Mander].

Service animals are another deductible medical expense, but we'll talk more about service dogs and other animal-related deductions on the next page.

Dog food is a serious expense, especially if you own a fat dog. So pet owners can be excused for looking for any possible deduction come tax time. But even though our pets perform many important services for us — chasing squirrels off the lawn, eating the leftovers under the baby's high chair — few of them qualify as professional service animals. If you do have a medical condition that can be helped by a service animal, though, then all pet expenses above 7.5 percent of your adjusted gross income are deductible [source: IRS].

Under certain conditions, your pet might qualify as a business expense. Let's say you own a farm and your cats perform a critical service as rat and mouse hunters that protect your stored grain. Or you own a junkyard and your dog is the best alarm system money can buy. In both of those cases, you may be able to deduct at least a portion of your pets' "maintenance" costs as a business expense [source: Kohler].

And then there's the case of the California "cat lady" who successfully wrote off her cat food as a charitable expense. No, she wasn't making charitable contributions to the cats. She argued in tax court that she was taking care of the cats for a nonprofit organization that found foster homes for feral animals. Even though the IRS denied the deductions, the tax court judge ruled in her favor [source: Saunders].

There are new changes to the next tax deduction that impact residents from Florida to Washington state.

The Internal Revenue Service (IRS) allows you to deduct state and local income taxes from your adjusted gross income during the same tax year. So, if you pay $1,000 in state and local taxes in April 2022 for income earned in 2021, you can deduct $1,000 from your 2021 federal income taxes.

But what if you live in a state like Florida, Texas or Washington that don't collect state or local income taxes? The IRS gives these taxpayers — all taxpayers, really — the option of deducting state sales taxes instead. The IRS offers a handy sales tax calculator for estimating your deduction, but you can take even larger deductions if you buy a boat, plane or an airplane [source: Mengle].

You can also deduct certain vehicle-related taxes. For example, many states charge an annual registration fee for your car, truck, motorcycle, motorhome or boat. This registration fee is really an extension of a sales tax, which is deductible as a personal property tax [source: Barton].

There is a cap, though. Your total claim for state, sales and property taxes cannot exceed $10,000, or $5,000 for married couples filing separately [source: IRS].

Here's another deduction that was amended by the 2017 Tax Cuts and Jobs Act. Starting in 2018, only self-employed filers can claim a deduction for tax preparation fees. To qualify for this deduction, you need to either be a self-employed worker who files a Schedule C, a farmer who files a Schedule F, or someone who earns income from rentals or royalties and files a Schedule E [source: Bird].

Deductible tax preparation expenses and fees include your accountant's fee, any software you purchased to help you prepare your taxes (online services like TurboTax count), and even "how-to" books about taxes [source: IRS]. If we charged you for reading this article, you could deduct that, too.

Another deduction that was eliminated in 2017 was the appraisal fee. Technically, the changes to the tax code made by the Tax Cuts and Jobs act expire at the end of 2025, so some of these itemized deductions could make a comeback in 2026 [source: Bird].