To start with, only some expenses are deductible. Medical expenses, but only if they exceed 8.5% or so of your adjusted gross income. Not clothing, unless it is clearly needed for work and not everyday clothes. Charity contributions, a few other things. The deal is, though, the standard deduction is so large these days that you need a huge amount in deductions before itemizing makes sense. If you're not paying mortgage interest and property taxes, it's hard for the average person to dig up enough in deductions to make it worth while. If are doing jointly, you need one 25000 in deductions before itemizing starts to make sense. It's how they simple tax filing a few years ago: they just gave everybody more in the standard deduction.