
Well, in fairness to him... I have been in financial services in NYC for my whole career, I'm a partner at a reasonably sized firm, and I have never been invited to a black tie event in connection with my job. These days it's pretty easy to go your whole life without wearing a tuxedo...
Not that it means he should be reimbursed. The objective way to resolve it is to answer the following question: would the IRS would consider it a deductible business expense for the company? In this case I highly doubt it.
I think the rule is that clothes that has a use outside of work is not deductible. So a UPS uniform that an employee has to pay for is deductible whereas a suit or tuxedo is not.




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