17 Crazy Tax Deductions That Were Actually Legit

Former President Donald Trump's tax returns — and his reported $70,000 deduction for hairstyling — once became a hot topic and got lots of people talking about what is and what isn't a legitimate tax deduction. From trying to write off breast enhancement to deducting the cost of at-home petting zoos, tax professionals have heard it all. We asked tax preparers for some of the most unusual, unexpected, or lavish deductions they've encountered over the years. And while these deductions may have worked in the past, today they might result in a quick visit from the IRS.

Related: Why Billionaires Pay Less Tax Than You

Using a clarinet to remedy an orthodontics issue is apparently a real form of treatment, and one that meets the approval of the Internal Revenue Service when it comes to tax deductions. Samuel Hicks, a CPA with Stern, Kory, Sreden & Morgan, said one of the quirkiest tax breaks he's come across is tied to a 1962 ruling from the IRS that allows deductions for the cost of a clarinet and lessons for playing it. "The only requirement is that an orthodontist should recommend the playing as a part of orthodontic treatment," Hicks said.

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If you can get your doctor to write a prescription for installing a pool or spa in your home, you might be able to write off part of the cost, said Janet Berry-Johnson, a CPA and tax expert for Money Crashers. "The key is the pool or spa has to be prescribed to alleviate or prevent a physical or mental illness or a medical condition." Unfortunately, since the pool or spa is also considered a capital improvement to your home, the entire cost of installation cannot be deducted. "You'd have to reduce your deduction by any increase to the value of your home that results from installing the pool," Berry-Johnson said.

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While you're unable to deduct the cost of weight-loss programs if you're pursuing the program merely for appearance or general health and wellness, if your doctor prescribes the program to treat a specific medical condition such as obesity, hypertension or heart disease, then the deduction is totally legitimate, Berry-Johnson said. "However, you still can't deduct special food or drinks or the cost of your gym membership," she added.

For business owners whose primary office or client meeting location is their residence, it may be possible to write off lawn care expenses, said Steve Sexton, financial consultant and president of Sexton Advisory Group, a California-based financial services firm. "This applies if the state of your lawn plays an important role in the performance of your business, such as acquiring and retaining clients," Sexton said.  

It's hard to believe, but babysitting fees can actually be deducted, said Chayim Kessler, a CPA with MiamiBeachCPA. "The Child Tax Credit is applied to your expenses for daycare or hiring a babysitter while you're at work," Kessler said. "However, if you're out of the house for reasons other than work, you cannot file babysitter's payments for credit because such expense goes to your personal use."

Through the home office deduction, you may be able to deduct the cost of painting your home work space, said Alexa Serrano, personal finance expert and banking editor for the website Finder. "How much you're eligible to deduct depends on whether you use the room exclusively for business." If the office is used entirely for business and nothing else, the entire cost of the paint is eligible for deduction as long as it doesn't exceed your total business income for the year. 

It may seem like a page out of a Hollywood movie script, but it's not unusual for businesses to be victims of ransom demands from cybercriminals. Hackers steal everything from customer lists to company secrets that can be sold to competitors. Whatever amount of ransom ends up being paid as part of such an incident is tax deductible. "If a business owner paid the ransom, the business can receive a tax deduction providing the business files a report with the SEC and local police. If the business owner did not file a report, the business cannot deduct the ransom," said Sexton, the California-based financial consultant.

Early in Donna Merrill's career, the small-business tax expert had a client who wanted to write off a petting zoo for a home-based direct sales business. The justification? Frequent home meetings with clients whose kids could be entertained by the animals. Merrill, founder of Business Untangled, asked a tax pro who told her to "position the deduction strategically on the tax return with very visible notes to be seen upfront." The advice worked. The deduction has been accepted by the IRS for many years. Merrill said you can write off almost anything in your business if you can prove it is an ordinary and necessary expense incurred in running your business. "It needs to support your profit intent," Merrill said.

As over-the-top as this deduction sounds, purchasing a jet can be a legitimate expense for a business. According to the regulations that were part of the Tax Cuts and Jobs Act, businesses that purchased a new or pre-owned jet and started using it before Jan. 1, 2023, could write off practically every cent associated with the purchase for the first year. However, businesses had to exclude any costs associated with using the jet for entertaining. 

Losing in Las Vegas or any other gambling mecca is rarely fun. But the good news is that the IRS allows for writing off some of those painful losses. Yes, you read that right. Those who itemize deductions on Schedule A and who kept a record of their winnings and losses may write off the losses. Good to know, right?

Traveling for work can have its share of pros and cons. But it's never fun when you show up for a work-related engagement on the road and your clothes are dirty, stained or otherwise less than presentable. The good news is that the IRS allows for deducting the cost of any dry cleaning or laundry you require while globetrotting for work.

While this deduction might seem like a bit of a stretch, it turns out that if you use services such as Spotify in the office to provide entertainment for people while they wait, or in a store where customers shop, it's legitimately deductible. "A business generally can deduct anything that's ordinary and necessary in the course of carrying on a trade or business," said Mike Kern, CPA and co-founder of Kore Talents. "The cost of a streaming service to provide a proper environment to your customers would definitely fit the ordinary and necessary requirement."

Looking good at all costs is par for the course in the entertainment industry, where appearance is definitely a factor in generating income. So, it stands to reason that some cosmetic surgery would be viewed as legitimate write-offs by the IRS. The main criteria is that the surgery can reasonably be expected to generate more income. Perhaps the most famous case of breast implants being claimed as a deduction was exotic dancer Chesty Love making the claim that bigger breasts would generate bigger tips. The IRS consented to the write-off, describing the breasts as a stage prop essential to her act.

The most interesting tax deduction CPA Logan Allec has ever written off on a client's return involved leather clothes, whips, and handcuffs. "This was for a dominatrix running a successful dungeon here in the Los Angeles area," said Allec, founder of personal finance site Money Done Right. "This probably goes without saying, but hers was a legitimate business. No sex or nudity was involved, only harm-free bondage." While Allec said there isn't a section of the tax code that specifically allows for whips and handcuffs as a deduction, the expenses fall under the general rule of Internal Revenue Code Section 162(a), which covers deductions for ordinary and necessary expenses paid or incurred in running a trade or business.

Paying your significant other to work for you may very well be legitimately deductible. In yet another filing that tested IRS limits, a taxpayer paid his live-in girlfriend to do everything from finding furniture to supervising repairs at various properties. The IRS initially balked at writing off the salary. The resulting clash ended with a court saying $2,500 of the $9,000 he paid her was a business expense, but paying for her housekeeping was nondeductible. "Paying someone to help manage rental properties or find furniture could be considered a business expense regardless of your relationship with the person you are paying," Allec said. "However, you cannot deduct the amount you pay your girlfriend to clean your house in the same way you cannot deduct the allowance you pay your children to do chores."

Most of us just have to live with annoying and pricey ATM fees. But if a business owner decides the best way to pay themselves is to take cash withdrawals out of an ATM that charges fees, those fees are tax deductible. "ATM fees for business accounts are deductible assuming the cash withdrawal was used for a business purpose," said Allec, of Money Done Right. "But obviously it'd be better to go to an ATM where you won't be charged a fee."

One last unusual deduction that ultimately was allowed, a couple who ran a junkyard claimed cat food expenses as a write-off. Their rationale? The food was used to attract cats and the cats controlled the snakes and rats in the junkyard. While the IRS balked at that, a Tax Court ruling allowed the deduction.

Related: These 13 States Still Tax Groceries