The U.S. Tax Code is huge -- more than 5 million words long. How is it possible to know the answers to all the wide-ranging tax questions, such as can dry-cleaning be deducted as a business expense? (Answer: No.) Can mortgage points paid when refinancing a mortgage be deducted? (Yes, but they must be spread out over the life of the loan.) Can educators deduct the unreimbursed costs of school supplies? (Up to $250 worth, even if the teacher doesn't itemize.) Can strippers deduct the costs of breast implants? (A full-figured yes.)

So, where do you turn for all the answers? Well, we have plenty of resources right here at the Fool, including our Tax Center, our Tax Strategies discussion board, and The Motley Fool Tax Guide.

We'll help out right now by discussing the broadest category of deductions: "Miscellaneous." First of all, you have to know that "miscellaneous" expenses can be deducted only to the extent that they, as a whole, exceed 2% of your adjusted gross income.

For example, take the case of Larry McCloskey, CEO of online meringue manufacturing and delivery company Larry's AGI amounts to $45,000. He has miscellaneous itemized deductions of $1,000, subject to the 2% limitation. Since 2% of Larry's AGI amounts to $900, his miscellaneous itemized deduction will be limited to $100 ($1,000 in total deductions less the 2% of AGI amount of $900).

Do you have enough miscellaneous deductions to cut your tax bill? Take a look at the following list of some (but certainly not all) of the most common miscellaneous itemized deductions subject to the 2% of AGI limitation:

  • Appraisal fees (for charitable donations or casualty losses)
  • Clerical assistance in order to maintain investments
  • Depreciation on business assets
  • Unreimbursed employee business expenses
  • Expenses to collect interest or dividends (collection fees)
  • Hobby expenses to the extent of hobby income
  • Work clothes and uniforms, if they are required by your employer and not suitable for outside wear
  • Tax preparation fees and/or other tax assistance expenses
  • Legal fees for collecting or producing taxable income, keeping a job, or obtaining tax advice
  • Professional fees for obtaining investment advice
  • Investment expenses in general and some investment travel
  • Job-hunting expenses
  • Safe-deposit box fees
  • Cost of a home safe to retain tax/investment papers
  • Small tools and supplies used in your trade or business
  • Retirement custodial fees paid directly (such as IRA, Keogh, SIMPLE, etc.)
  • Job-related educational expenses
  • Medical examinations required by your employer
  • Professional and union dues
  • Repayment of income (in some cases)
  • Service charges on dividend reinvestment plans
  • Trust administration fees
  • Long-distance business calls
  • Books, magazines, and other publications dealing with investments or taxes
  • Legal fees for the collection of alimony
  • Office-in-home deduction for an employee (self-employed folks are treated differently)
  • Office-in-home expenses for an employee (self-employed folks are treated differently again)
  • Job dismissal insurance
  • Extra cost of a phone installed in your home for business use
  • Business-related travel and entertainment

This is just a partial list. Hundreds of other miscellaneous expenses may apply to you. IRS Publication 529 will help you identify them. In addition, some of the items above are complicated and require additional research.

Now, let's take a look at a list of items not considered miscellaneous itemized deductions. There are many misconceptions regarding what is and isn't deductible in this section of Schedule A. Here's a brief list of many of the most commonly misunderstood items that don't qualify as miscellaneous itemized deductions:

  • Personal living expenses
  • Commuting expenses
  • Funeral expenses
  • Home repairs and improvements to your personal residence
  • Legal fees for divorce (other than for tax planning)
  • Parking tickets and other fines that are payments for illegal activities
  • Political contributions
  • Sales tax (except when added to the cost of a business asset)
  • Telephone expenses of the first line for basic local residential service (even if a portion of the use is for business purposes).
  • College tuition
  • Education expenses that qualify you for a new trade or business
  • Club dues (except for certain business or public service organizations)
  • Gambling losses in excess of gambling winnings
  • Licenses and fees (such as marriage licenses, animal licenses, driver's license, etc.)
  • Life insurance
  • Losses from the sale of your personal residence
  • Cleaning of your work clothes, if you wash them yourself (not professionally)
  • The cost of travel that is primarily a form of education
  • Costs directly related to buying or selling an investment (such as broker purchase and sale commissions)
  • Expenses and costs of attending investment seminars or conventions
  • Expenses to attend a company's annual stockholder meeting, even if you own stock in that company (unless you're organizing a hostile takeover)
  • Estate planning advice (except for the portion related to tax advice)
  • Legal costs and expenses relating to child support and custody

Still have questions? After looking through our resources, you could even check out the official IRS website.