“Alternative” medical expenses: A New York lawyer tried to write off over $110,000 he spent on prostitutes, claiming they were part of his medical treatment for osteoarthritis. No, said the IRS, on the basis of prostitution being illegal in his state of New York. Worth noting is that while the IRS from upon deducting (as a medical expense), the fees charged illegally by prostitutes, the IRS requires the prostitutes to pay taxes on the fees they earn.
Feeding and dressing your model child: A photographer tried to deduct the costs of feeding and clothing her child, claiming it as a business expense because she sometimes used her child as a model in her business. The IRS said no, allowing the photographer to deduct only the price of outfits the child wore in photographs for which the photographer was paid.
Too much fun to be deductible: A farmer wanted to deduct the cost of his ATV, claiming that he used it to “check the fence lines” on his property. His accountant felt like the off-roading seemed a little too fun to not raise red flags with the IRS, which it did. Deduction denied.
Source: Reader’s Digest