• It has been done.
  • Of course. I'm pretty sure waitresses, film stars and fitness instructors do also.
  • Yes, and their 'uniforms' too. As well as cosmetic surgery.
  • Probably, speak to an ex tax accountant they know every loophole.
  • I knew one who did it. I once had a summer job at a law firm that represented a number of strip clubs, and one of their headliners used a lawyer in the firm's tax and estate department to handle her taxes. She claimed the expense of her breast implants, and the IRS didn't balk. HOWEVER: it can take years for the IRS to decide to audit a return and disallow a claim, so it's possible that long after I worked in that job, the stripper in question had to repay at least part of her refund.

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