It’s standard career advice to dress for the job you want, not the one you have. But they never tell you how you pay for “boss clothes” on an underling budget. 

It’s only natural to try to get some wardrobe help on your tax return. Sadly, it’s easy to make a fashion mistake on your 1040.

Case Studies 

If anybody needs to look sharp, it’s TV anchors and actresses. The camera is unforgiving in a high-definition world, so thrifty wardrobe choices can stand out like a cheap suit. But the IRS has no fashion sense.

Anietra Hamper, a personality on a Columbus, Ohio, TV station, had to buy her own work clothes. She took a common-sense approach to her deductions, according to the Tax Court:

She would ask herself “would I be buying this if I didn’t have to wear this” to work, “and if the answer is no, then I know that I am buying it specifically” for work, and therefore, it is a deductible business expense.

An actress who was a stand-in for the Penelope Garcia character on the show “Criminal Minds” took a similar approach, according to the Tax Court:

Petitioner also claimed as business expenses items including makeup and beauty expenses, wardrobe expenses, and laundry and cleaning expenses. She claims that these expenses were necessary because of the unique dress and makeup of the character Garcia, according to the court.

Unfortunately, the tax law takes a different approach. IRS Publication 529 explains: “You can deduct the cost and upkeep of work clothes if the following two requirements are met:
• You must wear them as a condition of your employment.
• The clothes are not suitable for everyday wear.”

“It is not enough that you wear distinctive clothing. The clothing must be specifically required by your employer. Nor is it enough that you do not, in fact, wear your work clothes away from work. The clothing must not be suitable for taking the place of your regular clothing.

“Examples of workers who may be able to deduct the cost and upkeep of work clothes are: delivery workers, firefighters, health care workers, law enforcement officers, letter carriers, professional athletes, and transportation workers (air, rail, bus, etc.).

“Musicians and entertainers can deduct the cost of theatrical clothing and accessories that are not suitable for everyday wear. “ 

Conservative or theatrical 

In the case of our TV anchor, the court said that her studio outfits didn’t make the cut, even though she wouldn’t have purchased the items if she were, say, a welder:

“Although she is required to purchase conservative business attire, it is not of a fashion that is outrageous or otherwise unsuitable for everyday personal wear.,” the court ruled. “Given the nature of her expenditures, it is evident that petitioner’s clothing is in fact suitable for everyday wear, even if it is not so worn. Consequently, the Court upholds respondent’s determination that petitioner is not entitled to deduct expenses related to clothing, shoes, and accessory costs, as these are inherently personal expenses. Additionally, because the costs associated with the purchase of clothing are a nondeductible personal expense, costs for the maintenance of the clothing such as dry cleaning costs are also nondeductible personal expenses.

It might have been a closer call for our actress, but the Tax Court reviewer went thumbs-down:

“Neither petitioner’s records nor her testimony tied specific items of expense to the type of clothing and related items that would not be suitable for everyday wear. To the extent that items cannot be tied to petitioner’s job with “Criminal Minds,” her arguments about the uniqueness of Garcia are not persuasive.”

Not being much of a TV viewer, I can’t say whether a normal person would go out in public dressed like Penelope Garcia, though at least one commentator suggests one would not. Our actress needed to convince the judge that her purchases met the standard for “theatrical clothing and accessories that are not suitable for everyday wear.” Her performance in Tax Court failed to convince the relevant critic.

Neither petitioner’s records nor her testimony tied specific items of expense to the type of clothing and related items that would not be suitable for everyday wear. 

So what does the tax law tell the fashion-conscious aspiring boss?

First, that it’s difficult to deduct work clothes, and probably impossible for us cubicle monkeys. Even for actors and others, you need to be able to show the connection between your clothing purchases and your roles, and you need to have receipts to prove what your expenses are.    
Otherwise, your deductions might close early to a bad IRS review.

Joe Kristan is a CPA at Roth & Co. P.C. He first published this article on the Business Record’s blog