Question about a possible business expense

If you buy nylons for the sole purpose of masking your face during robberies, can you deduct them as a business expense?

"Provisions Denying a Deduction for Illegal Expenses and Expenses of an" by Douglas A. Kahn and Howard Bromberg.

It appears so. Exceptions are if the illegal activity is drugs or bribing officials.

So you have to be sure to declare the proceeds of the robbery on your tax return. Probably a good idea to ask the bank for a receipt as you are robbing them, and file that away carefully.

never mind

No, they would not be claimable as a business expense because they are adaptable to general usage. This applies regardless of the taxpayer’s personal preference in regard to wearing them outside of work. Of course, if the taxpayer were part of a gang and the nylons part of a gang “uniform” they may be deductible.

I always do.

Having worn a uniform for work most of my life. ETA: Although not with panty hose.

The deductibility of employee uniform expenses (on the now-nonexistent Form 2106) depended on them being unsuitable or suitable for ordinary wear. My dark blue uniform suit coat with the sleeve braid? Unsuitable for ordinary wear and hence deductible. The extra pair of dark blue matching dress slacks? Suitable for ordinary wear and not deductible. The white dress shirts with epaulet straps and weird pockets? Deductible. The white undershirts I wore only at work? Not deductible.


As to pantyhose specifically, that raises an interesting question. Assume it’s gang-required headgear during working hours. You could make a decent argument that for male gang members that would be a deductible employee business expense, while for female gang members it would not.

The reality about 1099 workers rather than W-2 employees is for the 1099 folks there’s a lot more room for questionable deductions to slip under the IRS’s notice. And now (gee thanks trump) that W-2 employee business expenses are not deductible, period, the only way to get this stuff deducted is as a 1099 worker or business owner / sole-prop yourself.

I think it’s important. If you are a robber with nonprofit status, it may be possible to reclaim income tax on the funds stolen, if you can establish that they were taken from a bank customer who was a taxpayer. Due to the fungible nature of the bank’s general cash float, this might only be applicable to robbery from safe deposit boxes.