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Wild and wacky tax deductions … and a few are OK by the IRS!

April 3, 2013

The hubby's favorite tax season chant — and, yes, he does just that each year as I work on our return — is "Deduct! Deduct!"

He even makes a few suggestions now and then.

But as creative as the hubby is, he's never come close to some taxpayers' really wild and wacky tax deduction attempts.

There's the nose job a wine connoisseur wanted to write off as a job expense. And then there's the profuse perspirer who was insistent that his air conditioning qualified as a medical deduction.

But my favorite is the pie shop owner who wanted to claim his restaurant meals because they included dessert, or as he called the lunch and dinner final courses, research and development for his own baked goods.

Cherry pie a la mode_Steve Snodgrass via Flickr
Cherry pie a la mode by Steve Snodgrass via Flickr

Sometimes such tax deduction chutzpah pays off for the taxpayer. Other times the Internal Revenue Service laughs all the way to the bank with the tax money it collects after denying crazy claims.

You can check out some of the more daring deductions at Bankrate, Business News Daily and CNN Money.

Some write-offs are legit. Others … well, let's just say that during tax filing season you can't blame a guy or gal for trying.

But regardless of their tax merits or success in taking on the tax man, all are entertaining.

Have you every trying to slip through an unusual tax deduction? Were you successful?

You also might find these items of interest:

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The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

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TAX-SAVVY WAYS 
TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

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