By Ken Berry, Esq.
A taxpayer in a new case, Reynolds, DC_NY, 12/8/25, tried to claim her golden retriever as a tax dependent. Naturally, she wound up in the district court’s doghouse. But that doesn’t mean the IRS and the courts won’t approve some unusual deductions.
As the 2026 tax filing season gets underway, take note of these seven “wild and crazy” deductions that have previously been allowed.
1. Pumping up the business. Generally, you can deduct the “ordinary and necessary” costs incurred by your business. But your business activity might be “out of the ordinary.” Take the case of an exotic dancer named Chesty Morgan. In an unpublished decision, Ms. Morgan was able to deduct the cost of obtaining breast implants as a legitimate expense that was considered ordinary and necessary for her trade (T.C. Summary Opinion 1994-79, 3/30/94).
2. A purr-fect deduction. As mentioned above, you can’t deduct the cost of food you feed your dog or other pet. However, in one case, a couple that owned a junkyard bought pet food to attract wild cats in the neighborhood. The cats took care of rats and snakes that were scaring away customers. At trial, the IRS conceded that the cost of the cat food could be deducted by the business (Seawright, 117 TC No. 24,12/18/01).
3. Strike a tax pose. Normally, you can’t deduct expenses that improve your looks or general health. But a professional bodybuilder deducted the cost of special lotions and body oils he applied before posing or working out. The Tax Court approved the deduction for this business expense. Key point: The products were specifically marketed to professional bodybuilders and not readily available to the public (Wheir, TC Sum. Op. 2004-117, 8/30/04).
4. Sweet tax music. This one comes straight from the IRS itself. To qualify as a deductible medical expense, the payment must be made for the diagnosis, cure, mitigation, treatment or prevention of disease or treatments affecting a structure or function of the body. In an historic 1962 ruling, the IRS agreed with an orthodontist that a child’s clarinet lessons were deductible because they helped correct the youngster’s overbite (IRS Revenue Ruling 62-210).
5. Doing a deep dive. Similarly, a taxpayer with arthritis argued that he could deduct the cost of installing an-ground pool. His physician had specifically prescribed swimming as an activity that could help alleviate his medical condition. The IRS approved but the deductible amount of the medical expense was limited to the difference between the cost and the increase in the home’s value attributable to the pool (PLR 8208128, 11/27/81).
6. Whale of a story. Going back to 2004, a whaling captain was able to deduct $10,000 in repairs, plus other equipment, to make the vessel ship-shape for whaling. Although this deduction is now restricted to certain Alaskan natives under the tax code (IRC Section 170(n)), you may be entitled to deduct boat repairs specifically required for a business operation.
7. Happy tax landing. If you’re fortunate enough to own a private jet, you may be able to deduct expenses relating to rental activities. In one case, a couple rented out their condo in Mammoth Lakes, California. They convinced the Tax Court that it was more efficient for them to fly from their home in San Jose on their private jet for management purposes than it was to drive or rely on infrequent commercial flights (French, 1990 TC Memo 314, 6/15/90).
The moral of the story? Don’t be afraid to think outside the box if you’re on firm legal ground.
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