The Art and Science of Successful Planning

creative tax deductions for individual

Creative Tax Deductions You Won't Believe

While Americans are entitled to claim every legitimate deduction available to them, the IRS places clear limits on creativity when it comes to write-offs. Some unusual tax deductions have actually been approved, while others pushed the boundaries a little too far.

Here’s a look at real examples of creative tax deductions that passed muster with the IRS, along with a few strange tax deductions that were ultimately denied.

Unusual Tax Deductions That Were Approved

Not every unconventional deduction gets rejected. In certain circumstances, the IRS has allowed some surprisingly creative write-offs.

Specialized School Costs as a Medical Expense

A child’s school-related costs typically aren’t deductible. However, one taxpayer was permitted to deduct the cost of travel, room, and board as a medical expense for sending a child with respiratory problems to a school in Arizona, where the climate supported the child’s health needs.

Pet Food as a Business Expense

Pet food generally doesn’t qualify as a tax write-off — except in one case where a business owner successfully argued it was a legitimate business expense, since the cat in question protected the company’s inventory from vermin.

A Clarinet as a Medical Deduction

If a child has an overbite, the IRS has allowed a medical deduction for the cost of a clarinet and lessons, since playing the instrument was shown to help correct the dental issue.

A Swimming Pool as Medical Treatment

A deduction for a swimming pool typically won’t hold up with the IRS — unless a taxpayer has a documented medical condition, such as emphysema, and is under doctor’s orders to improve breathing capacity through exercise. In such cases:

  • The deduction is limited to the cost that exceeds the resulting increase in property value.
  • Ongoing maintenance costs can also be deducted as medical expenses.

Creative Tax Deductions That Went Too Far

Not every unusual deduction attempt succeeds. Here are examples where taxpayers pushed the limits and were denied.

A Mink Coat for “Client Entertainment”

One business owner attempted to deduct the cost of a mink coat purchased for his wife to wear to client dinners, arguing it served as an integral part of the evening’s conversation and entertainment value. The deduction was denied.

Bath Oil for Dry Skin

Despite having dry skin, one taxpayer was denied a medical deduction for bath oil.

The “Loss of Memories” Deduction

Theft-related losses may be deductible in certain cases, but one taxpayer went too far by attempting to deduct the sentimental loss of memories after her photos and other personal keepsakes were discarded by her landlord.

An Arsonist as a “Consulting Fee”

In an especially bold attempt, one business owner reported an insurance payment as income, then tried to deduct the cost of hiring an arsonist by classifying it as a “consulting fee.”

Cosmetic Procedures for Self-Image

The IRS generally does not allow deductions for purely cosmetic enhancements. Examples include a ballerina who attempted to deduct a tummy tuck, and a taxpayer who tried to write off Botox expenses.

The Takeaway on Creative Tax Deductions

Creativity isn’t something the IRS typically rewards, so it’s wise to be cautious about testing the limits of what qualifies as a legitimate deduction. If you’re considering an unusual write-off, it’s best to seek guidance from an experienced tax or legal professional regarding your specific situation.

Frequently Asked Questions

What are some unusual tax deductions the IRS has actually allowed?

The IRS has approved several surprising deductions in specific circumstances, including travel and boarding costs for a child attending a specialized school for medical reasons, pet food for a business-guarding cat, a clarinet used to correct a child’s overbite, and swimming pool costs tied to a doctor-prescribed medical treatment.

Can you deduct pet expenses on your taxes?

Generally, pet expenses aren’t deductible. However, in one notable case, a business owner successfully deducted cat food as a legitimate business expense because the cat served a functional role in protecting the company’s inventory from vermin.

Why was the mink coat deduction denied by the IRS?

A business owner attempted to deduct a mink coat purchased for his wife to wear during client dinners, arguing it added entertainment value to business conversations. The IRS denied the deduction, as it didn’t meet the criteria for a legitimate business expense.

Are cosmetic procedures tax deductible?

Generally, no. The IRS does not allow deductions for elective cosmetic procedures aimed at improving self-image, as demonstrated by denied claims involving a tummy tuck and Botox treatments.


If you’re exploring deductions that fall outside the ordinary, working with a tax professional in Fort Myers or elsewhere in Southwest Florida can help you understand what’s truly deductible under current IRS rules before you file.

This material is not intended as tax or legal advice and may not be used for the purpose of avoiding federal tax penalties. Please consult a qualified legal or tax professional regarding your specific situation.

We also welcome you to a complimentary one hour consultation (no strings attached and zero obligation).

Please complete the form below to be scheduled for your complimentary consultation


Scroll to Top