5 Ridiculous Purchases You Won’t Believe Are Tax Deductible

boy playing clarinet
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Tax season is here, so thoughts naturally turn to finding ways to save money. While most people stick to standard deductions and predictable write-offs, others dig into more creative — and completely legal — options.

Here are some of the quirkiest deductible expenses that might make the average filer double-check the rules, according to AARP. These purchases show how thinking outside the box — while staying within the rules — can make a surprising dent in a tax bill.

Clarinet Lessons

In 1962, a parent was able to deduct the cost of their child’s clarinet lessons and the instrument itself, after they were prescribed by an orthodontist to fix the child’s overbite, according to a report by Boston University School of Law.  Unsurprisingly, it initially went to court, where it was ruled that it qualified as a legitimate medical expense (despite not being the most traditional treatment). It’s not always about prescriptions or surgeries — sometimes, even clarinet lessons can count.

Cat Food

Cats acting as unofficial exterminators in businesses like junkyards or warehouses aren’t just appreciated — they’re a deductible asset. In the case of Seawright v. Comm’r of Internal Revenue, a junkyard owner in 1995 successfully deducted the cost of cat food as a business expense, arguing the strays being fed were protecting the business by keeping rodents at bay. The court agreed, recognizing the vital pest control function that the cats performed and ruling the expense a valid one.

Guard Dogs

Cats aren’t the only animals on this list. Think about businesses that handle cash or high-value inventory and what they have to do to protect their assets. Fancy alarm systems and surveillance cameras might seem more obvious tax write-offs, but it’s not just electronic security that counts. According to Nolo.com, a guard dog also falls into the protection category. Expenses related to its training, care and food can all be written off — as long as the animal is there for purely business purposes, not as a pet. Don’t forget that size and breed matter here. A Chihuahua likely won’t cut it.

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Breast Augmentation

Cosmetic surgery typically doesn’t qualify as a deductible expense, but there’s an exception for those working in certain types of entertainment. If the procedure is deemed necessary for the job — such as enhancing a performer’s appearance to fit their role — it can be written off as a business expense. The Los Angeles Times reported in 1988 that an “exotic dancer” claimed a deduction for her breast augmentation surgery, arguing the implants were necessary for her career and the court sided with her. They even allowed the cost to be depreciated over time, treating it as a professional investment.

Costumes for Performers

Outfits used in a professional capacity, such as costumes for entertainers, are deductible as long as they aren’t suitable for everyday wear. Think Elvis jumpsuits, mascot costumes or other eye-catching attire. For entertainers, saving those receipts can turn a pricy wardrobe into an opportunity. That glitter-covered suit might not fit in at the grocery store, but it could save someone money at tax time.

Keep Everything Well-Documented

Every one of these quirky write-offs comes with the same caveat: thorough documentation is essential. Taxpayers need receipts, letters from professionals or other proof that these expenses are directly tied to their work or medical condition. Without sufficient evidence, the IRS is unlikely to approve the deduction.

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