1. Bingo losses
Even if you’re only a casual gambler, your winnings are fully taxable as income. So it only makes sense that you can claim gambling losses up to the amount of your winnings as an itemized deduction.
2. Breast enlargement
While you can’t include optional cosmetic surgeries in your deductible medical expenses, there are exceptions. You can include the amount you pay for breast reconstruction after a mastectomy because it’s considered medically necessary to fix a deformity related to a disfiguring disease.
3. Pregnancy tests
Many expenses related to having or not having children are deductible, assuming your overall medical expenses exceed 10 percent of your gross income (check with tax professionals). You can include the amount you paid to buy a pregnancy test kit, the same way you can with a legal abortion, sterilization, birth control pills (if prescribed by a doctor), or breast pumps.
4. Pet moving
Most people know that you can deduct moving expenses when they are job related, but few know that you can also deduct the cost of shipping your household pets to your new home if the move is related to your employment.
As a medical expense, you can also include the cost of wigs if a physician recommended them for your mental health after losing your hair to disease.
6. Clarinet lessons
The IRS has allowed people with an overbite to deduct clarinet lessons if used to treat the dental condition and if the lessons have been prescribed by a doctor.
7. Whale hunting-related expenses
You can deduct whaling expenses paid during the year to carry out whaling activities as a charitable contribution, with caveats. The Alaska Eskimo Whaling Commission must recognize you as a whaling captain and your deduction can’t exceed $10,000 a year.
You can deduct the cost and upkeep of work clothes if they’re required for employment and if the clothes aren’t suitable for everyday use. Delivery workers, firefighters, health care workers and professional athletes can all use this deduction. Musicians and entertainers can also deduct the cost of job-specific theatrical clothing and accessories.
9. Programs to stop smoking
Any program to help you stop smoking qualifies as a deductible medical expense, but you can’t include non-prescription items such as nicotine gum or patches.
10. Weight-loss programs
You can deduct expenses related to losing weight as long as they’re treatments for a specific disease as diagnosed by a physician, such as obesity, hypertension or heart disease.