Home & Garden Home 9 Nutty Tax Write-Offs That Work By Matt Hickman Writer Emerson College The New School Matt Hickman is an associate editor at The Architect’s Newspaper. His writing has been featured in Curbed, Apartment Therapy, URBAN-X, and more. our editorial process Matt Hickman Updated January 08, 2019 There are several tax-write offs that may surprise you...even swimming pools!. Doubletree Studio/Shutterstock Share Twitter Pinterest Email Home Thrift & Minimalism Pest Control Natural Cleaning DIY Family Green Living Sustainable Eating For those of you in the deepest of denial, a brutal reality check: Tax season is in full swing and the deadline isn’t that far off. Still there? Hello? For those who we haven’t scared off and sent into a full-on receipt-gathering panic attack, you’ll want to read on to learn more about nine of the oddest and most obscure tax write-offs on the books. Ranging from mammary-related business expenses to baby sitting as a charitable donation, most of these eyebrow-raising write-offs — by the way, they all “worked” and/or are legit although some were challenged by the authorities — may throw even the most seasoned tax professional for a loop. Who knows, maybe you qualify for one. So all you bodybuilding whaling boat captains with overbites or junkyard-owning feral cat-feeders who had reverse vasectomies in 2011, pay close attention. Baby sitters Take note, philanthropic night owls: Although there is an existing childcare tax credit of up to 35 percent that many qualifying families take advantage of, you can also deduct baby sitter-related expenses for instances when you’re not working or looking for work so long as you’re spending that time away from home volunteering for a charitable organization or nonprofit group. And to be clear, volunteering for a charitable organization or nonprofit group does not entail dinner at the Cheesecake Factory followed by catching the new Judd Apatow movie with the hubby. Body oil Just as a painter cannot work without a canvas or an actress without inspiration, the same could be said of a body builder and big ol’ tubes of body oil. In one of the more eyebrow-raising deductions in the annals of tax oddities, a professional muscle man from Wisconsin was triumphant in writing off body oil and tanning products as legitimate business expenses as they helped his bulging pecs and inhuman biceps glisten and glow under the bright lights during competitions. The oil-slicked hulk also tried to deduct the thousands of dollars spent on protein-heavy buffalo meat from his taxes — apparently, he ate a lot of it — but the tax court didn’t let this one fly. Breast enlargement There’s no doubt that with every profession comes oft-indispensable tools of the trade that can be deducted — or attempted to be deducted — as business-related expenses when tax season rolls around. And when you’re an exotic dancer from Indiana who goes by the name of Chesty Love, those tools just happen to be your freakishly oversized (10 pounds each) mammary glands. Ms. Love — birth name, Cynthia Hess — underwent two breast augmentation procedures that increased her already ample bust size to a 56FF and then to a 56N in order to, well, make bigger tips even though her breasts were a constant source of humiliation and hindrance in her offstage life. Love was allowed to write off her “stage props” by the tax court after going to battle with the IRS in 1994. Naturally, she appeared on “Jerry Springer” to discuss her legal battle. Cat food Canned food helps hydrate your kitty. correct pictures/Shutterstock Sure, no problem, you can totally deduct cat food from your yearly taxes ... but only if it’s exclusively offered up to the clowder of feral felines that roam your salvage yard. Meet Samuel and Carol Seawright, the proprietors of Columbia North East Used Parts in Columbia, S.C., who deducted hundreds of dollars in cat food as an "ordinary and necessary" business expense under IRS code section 162. The 1995 deduction landed the Seawrights in tax court a few years later, but the court ultimately permitted a $300 allowance for the cat chow as it was used to attract and feed the stray cats that kept the couple’s auto scrap yard free of cosumer-scaring vermin like rats and snakes. And while we’re on the topic of junkyards, yes, you can write off the costs of keeping a guard dog as a business expense but only if the pooch is used solely to protect inventory, livestock and the like and not kept as a pet. The IRS will want to know the breed of the dog — Dobermans, rottweilers and German shepherds all pass muster — so don’t bother writing off expenses associated with a yappy Maltese. Clarinet lessons This one is a tax law legend: In 1962, the IRS approved the deduction of clarinet lessons (and the clarinet itself) as a legitimate medical expense after the orthodontist of a young patient suffering from overbite recommended that she give woodwind instruments a go as a method of correcting her unsightly dental abnormality. Although this one certainly takes the cake when it comes to odd medical-related write-offs, IRS Publication 502 lists several others deductible expenses that might be overlooked: artificial limbs and teeth, support stockings, acupuncture treatment, pregnancy tests, vasectomies (and reverse vasectomies), breast pumps and wigs for those who have lost their hair due to a disease. Non-deductible items include electrolysis, diaper services, maternity clothes, dancing lessons and controlled substances. Pet relocation fees Although the moving-related tax deductions outlined in IRS Publication 521 are rather headache-inducing, some fabulous news for pet owners who have to relocate for reasons of employment: You can write off the costs of shipping/transporting Princess Tiddlewinks from Tampa to Tacoma along with other moving expenses as your pet, be it goldfish, iguana or Great Dane, is considered to be a personal effect. Sex toys and naughty lingerie According to a 2006 taxation law in Australia, prostitutes, strippers and others whose work can best be described as “erotic” are allowed to deduct items such as condoms, lubricants, gels and tissues as work-related expenses during tax season. Adult industry workers Down Under can also claim the replacement and repair of “fetish equipment” and “adult novelties” along with dance classes (“to maintain your existing dance skills or to learn new dance skills”), stage makeup and lingerie. However, fitness-conscious escorts and exotic dancers in Oz looking to write off that home rowing machine along with a bottle of strawberry-scented massage oil are out of luck as the law explicitly states: “You cannot claim a tax deduction for the cost of maintaining your general fitness and body shape.” Swimming pools Ever fantasize about deducting that backyard swimming hole and all of the expenses (chemicals, cleaning, heating, etc.) that come with it? It’s certainly possible but you should expect to tread some serious water with the IRS first. In one famous case, a man suffering from emphysema was advised by his doc to get more exercise. So, as anyone in their right mind would do, he went about constructing a private swimming pool and deducted it (less the increased value of his property) from his taxes as a necessary medical expense under IRS Publication 502, which states that such expenses may include “special equipment installed in a home, or for improvements, if their main purpose is medical care for you, your spouse or dependent.” The IRS resisted but the tax court sided with the pool-builder as he was able to prove that it was being used only for medical rehabilitation purposes and not for hosting neighborhood luaus. Whaling supplies Although commercial whaling is virtually banned in the United States, those who are allowed to partake, indigenous Alaskans certified by the Alaska Eskimo Whaling Commission, enjoy generous tax deductions of up to $10,000 on whale hunting-related expenses including money spent on boat repairs, fuel, weapons such as harpoons and grub to feed the crew. The late Sen. Ted Stevens (R-Alaska) and Sen. Lisa Mukowski (R-Alaska) were responsible for ensuring the success of this rather obscure provision to the tax code in 2004. And by the way, subsistence hunts of bowhead whales in Alaska are anything but lucrative, business-minded ventures. Rather, the seasonal hunts are a time-honored cultural tradition in which a small number of whales are killed.