Charitable giving is good for your tax return as well as your heart. Though you usually need a receipt, in certain circumstances you can still claim a deduction without one. However, if you don't have the proper documentation, you'll find yourself in hot water if your return gets audited.
TL;DR (Too Long; Didn't Read)
The IRS allows for donations of $250 or less without receipts only when it is impractical to get a receipt.
As a general rule, you need to get a receipt to claim a deduction for your donated goods. However, no receipt is required for donations valued at less than $250 when it is impractical to get one. For example, if you leave a donation of clothing valued at $100 at a charity's unattended drop box, you can claim a deduction even without a receipt. However, if you drop clothing off at the charity itself, you need to get a receipt.
Other Records to Keep
If you do drop off your donation where it's impractical to get a receipt, you still need to keep your own records to document the donation. Write down the name of the organization you donated to, the date and location of the donation, and a description of what you donated. You also need to write down the fair market value of the donated items as well as how you figured the value, how much you paid for the items, and the amount you are claiming as a deduction.
If you make a monetary donation of less than $250, you can prove your donation with a bank record or payroll deduction record if you don't have a receipt. The $250 limit applies to the amount of each contribution. For example, if you donate $100 every week to your temple using a check, you can prove the deduction with canceled checks. However, if you make just one $300 cash donation, you can't claim the donation as a deduction without a receipt.
If you pay expenses out of your own pocket for the charity, you can include those contributions as part of your deduction. You always have to have records to prove these expenses, but if your expenses are under $250, you don't need a receipt. Your records have to be made at the time you incur the expense. For example, if you want to write off mileage driven for a charity, you can't wait until the end of the year and guess at your mileage. Instead, you must keep records of the miles as you drive them.
Mark Kennan is a writer based in the Kansas City area, specializing in personal finance and business topics. He has been writing since 2009 and has been published by "Quicken," "TurboTax," and "The Motley Fool."