Here are a few deductions you may want to consider while you're scrounging for crumpled receipts. They've worked at least once, although we can't guarantee they'll work again...
1. Fancy dresses… but only if they're so tight you can't sit in them. Celebrity Dinah Shore claimed some formal dresses on her tax return, and, as you might suspect, the IRS immediately cried foul. Dinah explained that the frocks were business expenses; she only wore them on her television show and couldn't possibly wear them for personal reasons because they were so tight she couldn't actually sit down in them. But the last laugh was on Dinah. Though the IRS agreed to let her deduct the dresses, legend has it they sent a representative to judge which dresses really were too tight to sit down in.
2. Boobs. This one's pretty tough to deduct, but at least one person has done it—a woman named Cynthia Hess, AKA exotic dancer "Chesty Love." When she upgraded to size 56-FF breasts, she claimed them on her tax return as a necessary job expense. When the IRS said no, Chesty's lawyers went to court. They said that if she didn't have breast implants, she would actually lose money to other dancers. The court agreed, and Chesty got to deduct her enhancements.
3. Ostriches. Well, it's really the depreciation of any type of livestock, as long as its used for breeding purposes. Most people tend to write off depreciating technology, like computers and printers. An ostrich farmer in St. Tammany Parish, Louisiana, was apparently aware of the livestock law and used it to legally include the depreciation of his herd.
4. Body Oil. Are you a professional bodybuilder? If so, feel free to write off all of the products you use to keep your muscles looking spectacular during competitions. If the expense is "ordinary and necessary" for your profession, you're allowed to write it off.
5. Sex toys. Australia took the decidedly unusual step in 2006 of allowing prostitutes, strippers and other members of “the sex industry” to deduct the cost of buying sex toys. According to MSN, deduction privileges were extended to a wider range of sex-related items than just the toys, including but not limited to “condoms, lubricants, gels and oils.” That said, Australia made sure to stop short of going too far with its strange new deduction allowances. While Australian officials saw nothing wrong with strippers deducting explicit sex toys, they evidently could not stomach the thought of dancers writing off the exercise bikes or elliptical machines that kept them in peak performing shape.
6. Clarinet Lessons. A doctor recommended that a patient take up the clarinet because the way the instrument is positioned in the mouth lessens the pain of an overbite. The patient's parents bought him a clarinet and paid for lessons, which they were then able to take as a deduction since it was, in fact, a medical recommendation.
7. Cat food. When is cat food a deduction? When the cat is a business expense. Not just one you let roam around your bookstore, but one that actually earns its keep. A couple who owned a junkyard claimed their kitty was essential for keeping the property snake-and-rat-free, making it safe for their customers. The IRS said no way, but the reasoning passed muster when it was taken to Tax Court.
8. Beer. When a gas station owner offered free beer to his customers as part of a promotional deal, he deducted it as an essential business expense. Perhaps the IRS employees who reviewed his paperwork were enjoying some suds themselves, because the deduction was approved.
9. Swimming pool. In a situation similar to the clarinet lessons, a man was advised to start an exercise plan to improve his emphysema. Instead of joining the Y like most people would do, this guy installed a swimming pool, then tried to take it as a deduction on his taxes as a medical expense. It was approved - as were the cost of the chemicals, the cost to heat the pool, and the cost to insure the pool.
10. Amish Buggy. Well, it wasn't the buggy that was questionable—it was used for business and is a legitimate expense. It was the tricked-out accessories the young Amish man wanted to include on the write-off: dash lights, kick plates, tinted windshield, speedometer, hydraulic brakes and dimmer switches.