Scarlet Meyer
Updated March 26, 2017
Overture Films

April 18th, or as it is better known, “Tax Day,” is almost upon us. While this usually means scrambling around trying to find lots of random papers, right now we’re finding ourselves laughing. Why would we be laughing when the deadline to file taxes is almost here? Probably because we’ve run into a bunch of the craziest successful write-offs we have ever seen, and they’re hilarious as they are inspiring!

So just a disclaimer, these are not only real, but they totally worked!

So without further ado, here are nine real and totally wacky tax write offs that the IRS approved:


If your clothing is part of a uniform or work outfit, you might be able to write it off. According to the two tax professionals in an interview with Money, this is seen a lot with people like Elvis impersonators. It’s pretty easy to see why they would need their outfit specifically for work. (Although we would argue Elvis outfits are great to have just, because, too.)

Apparently, one of the more famous examples was actress Dinah Shore. She wrote off some of her clothing on her taxes because she claimed it was so tight she couldn’t sit down. Therefore it was purely for television work, not for every day use!

A tropical vacation!

An article from TurboTax describes how a lot of Caribbean locations such as Bermuda, Barbados, and Costa Rica can be counted as a tax write-off, if you go for business. This also works for the US, Mexico, and Canada, but why not spring for a tropical location? Weirdly enough, you can’t pull this off in every place though. For example, trips to Paris, Rome, and Beijing cannot be written off unless you can prove it only made sense for the meeting to be specifically held there!

Breast implants!

This falls in again with “if you can prove it’s for work, you can write it off!” According to Forbes an exotic dancer named “Chesty Love” was able to write off her breast implants, arguing that they were purely for work, and that they helped her increase profits as a dancer! Since she was able to prove she was right, she got to write them off!

Gambling losses!

Weirdly enough, you can sometimes write off your gambling losses. According to Money, you have to be super specific about it though, and make an itemized list of how much you lost and where, when, and who you were with. Honestly, if it was us, we probably wouldn’t want to think about it, but if you’re able to pull this off, more power to you!

Clarinet lessons!

This one was super strange, but according to the Los Angeles Daily News someone was able to write off clarinet lessons! How did this work exactly? Apparently there is a lot of leeway in write-offs when it comes to medical expenses. Since this client had a doctor recommend they take clarinet lessons to fix an overbite, they were able to write them off.

Swimming pools!

Similar to the clarinet lessons, if a doctor recommends you start swimming more for your health, you can write off building a swimming pool! According to Forbes, a patient with emphysema wrote off a swimming pool after their doctor ordered them to start an exercise regimen. Luckily for them the tax court allowed the write off! We’re hoping our doctors ask us to sit around in jacuzzis more! (You know, for our health!)

Free beer!

TurboTax shared an amazing story of how a gas station owner was able to justify giving away free beer in his write-off. By demonstrating that it improved his business and brought in more customers, he got IRS approval for maybe one of the best write-offs ever.

Your significant other!

TurboTax also describes how one real estate broker was able to write off paying his girlfriend. Apparently, he wrote off money he gave to his live-in girlfriend to manage some of his properties. While he only won the right to partially write off the money, it is still pretty amazing.

Body oil!

Apparently, Forbes reported that pro body builder Cory Wheir was able to write off body oil on his tax return! It seems crazy, but it is totally true, as for him, all that glistening oil was technically a business expense.

Obviously, these crazy tax write-offs are very “DO NOT TRY AT HOME W/O A REPUTABLE ACCOUNTANT DOING IT LEGALLY.” These are extremely rare cases and circumstances, and again, should never be attempted without an accountant backing you up. Still, it gives us hope to know that one day, we too, might be able to write off a vacation!