Strange Tax Deductions That Pass the IRS Test

pcmag.com:

Imagine being an IRS auditor and having to scrutinize business deductions in the taxes of the self-employed. A business coach deducts 30 percent of her honeymoon costs. A doctor claims his streaming service subscriptions (Amazon, Netflix, and Hulu) are business deductions. A parent deducts the cost of a clarinet and clarinet lessons for her child. An exotic dancer takes a deduction for the cost of her breast augmentation.

Far-fetched as these may sound, they've all been claimed on taxpayers' 1040s. One—the exotic dancer "Chesty Love"—prevailed in her 1994 court case, Reginald R. Hess and Cynthia S. Hess v. Commissioner of Internal Revenue. Hess maintained that her size 56N implants were "stage props" that increased her earnings and that she derived "no personal benefit from them." 

The court found in favor of Chesty stating in its ruling that her "extraordinarily large" implants were "useful only in her business." Originally submitted to the court as $2,088 of depreciation on a deductible business expense (Schedule C), she was eventually granted a Schedule A deduction (medical expenses) for the full cost of the implants, $5,368. 

As for the honeymooning business coach, she deducted a percentage of her rental costs for an Airbnb, business meals, and the costs of photography equipment she used for doing brand and content shoots. The doctor streamed content in his office waiting room for nervous patients. And the parents were told by a medical professional that playing the clarinet might help correct their daughter's overbite.

You couldn't make up the expenses some people have actually tried to claim on their income taxes. If you use one of the best online tax software prep services, it might suggest deductions that you