11 goofy, but legal, tax deductions

March 8, 2009

Every year as I work on our tax return, the hubby offers words of encouragement. Well, it's not exactly encouragement; more like an insistent plea.

And it's really just one word, repeated several times: Deduct!

I long ago gave up my automatic response of explaining why credits are better that deductions. He knows by now that deductions only reduces your potential tax bill incrementally, based on your tax bracket vs. the dollar-for-dollar cut of your IRS bill that comes from credits. Sorry. Just had to sneak that in.

But there's just something about the deduction process that is so appealing.

Maybe it's because there are so many possible ways to deduct. Or maybe it's a way to express our ingenuity and creativity before one of the potentially harshest judges, the tax man.

Regardless of the motivations, exploring all the possible ways to deduct something on your taxes remains a popular filing season exercise.

11 oddball deductions: Kiplinger.com takes a look at the lengths to which people will go to find an allowable deduction.

Free beer sign (2)
They range from some that a lot of folks legally claim each year, such as the cost of moving your pet when you relocate, to some downright jaw-dropping expenses, such as free beer and breast enlargement.

True, in the most odd of deduction claims, the taxpayers had to fight for their right to write off the costs in tax court. But they won.

Here's the magazine's list of 11 off-the-wall, but ultimately approved, claims:

  1. Pet food

  2. Moving the family pet

  3. A trip to Bermuda

  4. Body oil

  5. A private airplane

  6. Babysitting fees

  7. Breast augmentation

  8. Landscaping

  9. Free beer

  10. Swimming pool

  11. Girlfriend

Kiplinger.com details exactly why the taxpayer prevailed in these 11 weird write-off situations.

You and I might not have the exact same set of tax circumstances to convince a judge, but at least we can enjoy the resourcefulness and chutzpah of these taxpayers and their oddball deductions.

Order the Free Beer! poster from AllPosters.com

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Tax Season 2026 Continues!

We made it. Tax Day 2025 is finally over. For most of us. When the filing season started on Jan. 26, millions who were expecting refunds filed immediately. Most of us got our returns to the Internal Revenue Service by April 15. But plenty of taxpayers also got extensions. They are looking at an Oct. 15 filing deadline.

Those procrastinating filers aren’t a problem. In fact, the IRS appreciates taxpayers who take time to fill out their 1040 forms correctly. It also is grateful that tax submissions are spread out a bit, especially now that the IRS is a leaner agency. Processing returns is easier when they arrive throughout the year instead of in massive bunches.

But enough about Uncle Sam’s tax collection issues. The focus now is on all y’all who filed for extensions, giving you another six months to complete your return. Since your new mid-October due date will be here before you know it, let’s get started now on meeting it.

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Comments
  • TaxRascal
    17 years ago

    The babysitting fees deduction is actually pretty clever. Letting someone deduct the expenses associated with charitable contributions is probably sensible (especially since they recoup some of that by taxing the sitter’s income).

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