Whether you've got a shoebox full of receipts or a laundry list of write-offs, keeping your itemized deductions in order is key to cashing in during tax time. YNN's Tara Lynn Wagner filed the following Money Matters report.

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To itemize or not to itemize? When it comes to filing your taxes, that's often the question. The answer is strictly a mathematical one, based on your filing status.

"For example, a person who is single would claim $5,800 of a standard deduction this year so if they have itemized deductions worth more than that, it's worth the itemization," says H&R Block Tax Associate Wilma Hayes.

Most of the common deductions can be found on Schedule A, including mortgage interest and state and local taxes. But experts say there are plenty of common items that are commonly overlooked. Take for instance medical expenses, which have to exceed 7.5 percent of your adjusted gross income to qualify. While the obvious would be doctor fees and prescription drug costs, CPA Jay Safier says there are a host of deductible items that could fall into this category.

"There's equipment, wheelchair, hearing aids, eye glasses, batteries for the hearing aids. If you had to travel out of town for a hospital and you had to stay in a hotel, you can deduct the lodging up to I think $50 a night," says Safier.

Medical expenses for your dependents may qualify as well, but human dependents only. Vet bills and pet meds don't count.

"Dogs are man's best friends but they are not deductible," adds Safier.

Next up: Gifts to charity, monetary or otherwise. Two things to be aware of here. One, only donations to specific organizations are eligible. And two, if you're claiming anything over $250, you'll need a record of that donation.

"You need to make sure that the charity has been approved by the IRS as 501c3, you know, that it's tax exempt," says Hayes.

If you're donating goods like used clothing, consider making a trip to the charity's office. Drop boxes are convenient but they don't give receipts, so at the very least, you'll want to snap a picture of the process just in case the IRS comes calling for proof.

Finally, any unreimbursed job expenses can also be deducted -- from uniforms and union dues to wining and dining clients. And, if you're paying a professional to add up your deductions for you, well, their fees are deductible too.