5 Weirdest Tax Deductions That Are Actually Legit

Editors' pick: Originally published Feb. 27.

This time of year, we are all scrambling to tally our 2016 deductions so we can get that tax bill down. And while you're counting the obvious stuff, like charitable contributions and business meal receipts, there are a ton of deductions that are just not that apparent. 

And there are a bunch that are just plain weird. So weird that by no means are they a sure thing for everyone, so please talk to a professional before you attempt to deduct this stuff.

Here are five bizarre deductions.

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5. Swimming Pools
5. Swimming Pools

The big hole in the ground that swallows money actually may be deductible if your doctor prescribes its installation for your health. So if you are ill or arthritic and your physician advises swimming to treat your condition, the costs of installing that pool are deductible.

But only to the extent that the cost of the pool exceeds the value that it adds to your home, says Lisa Greene-Lewis, CPA, communications manager and tax expert at Intuit.

So let's say that your pool costs $25,000 to install and it increases the value of your home by $10,000. You only can deduct $15,000 as a medical expense ($25,000 - $10,000).

Remember that medical expenses are deductible only after they exceed 10% of your adjusted gross income (AGI). So if your AGI is $75,000, the first $7,500 of medical expenses don't even count. Anything above that is deductible. (Use 7.5% if you're 65 or older.)

4. Whaling Boat Repairs
4. Whaling Boat Repairs

If you are a whaling captain, recognized by the Alaska Eskimo Whaling Commission, and you carry out sanctioned whaling activities, you may be able to deduct up to $10,000.

This deduction includes repairs, equipment purchases, and other expenses associated with the business.

And the weirder part is that this deduction is considered a charitable contribution, not a business expense, even though there is nothing charitable going on here.

And just because you loved Free Willy, don't think you can take your entrepreneurial spirit to the ocean and become a whaling captain and grab a $10,000 deduction. Whaling is banned by the United States government, and only Native American tribes are allowed to engage in it. 

So this deduction basically is for the Alaskan Eskimos because whaling is a part of their culture. (And it's so darn cold up there, they deserve something extra.) 

3. Clarinet Lessons
3. Clarinet Lessons

While there's not much worse than listening to a fourth grader practice the clarinet, if she has to play to straighten her teeth, then the cacophony becomes much more melodious since you now will get a tax deduction for it.

"If your doctor prescribes playing the clarinet as the solution to your child's overbite, then the instrument and any necessary lessons are deductible," says Greene-Lewis.

So buy earplugs and be grateful that you may dodge an orthodontist bill.

2. Exceptional Tree Deduction
2. Exceptional Tree Deduction

Yes, some trees are exceptional. And if you have one on your property in Hawaii, you can deduct up to $3,000 per "exceptional tree" for qualified expenses you incurred to maintain that tree.


An exceptional tree is "a tree, stand or grove of trees with historic or cultural value, or that by reason of age, rarity, location, size, aesthetic quality or endemic status, is designated by a county arborist advisory committee as worthy of preservation," according to Hawaiian legislature.

So have a local county arborist look at your trees out in Hawaii. And then maybe you can deduct all expenses that are "reasonably necessary" to maintain those tree.

Even Mother Nature offers deductions now.

1. Breast Implants
1. Breast Implants

You knew this was coming. In 1994, a stripper claimed she needed breast augmentation surgery to get more tips. She actually had a few breast surgeries at the behest of her manager and ended up a size 56N. Um...yeah.

So in addition to increasing tips, she was offered multiple TV appearances and was able to participate in "freak-size people" shows around the world. Read the legal doc. Her business ballooned as a result of her surgery.

And the IRS agreed. A bunch of court hearings later, she claimed her, um, assets, were a stage prop and she was able to deduct the costs, because they were used in "her trade or business and she derived no personal benefit from them." 

We're presuming the judge spent ample time understanding her stage props before he made his decision.

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