I should admit to something here... my clothing is generally picked (or at least assistance comes from) my girlfriend, because I trust her taste sometimes more than my own (I am a math major after all). Heh heh. And I regularly shop ebay trying to find deals on good suits, although it looks as though the 3-piece I just grabbed might be a piece of crap, and it was $300. The formulae I used to determine offset of depreciation by interest gained on investment are at home, and I am at work (supposed to be working rather than posting on a style forum). Basically, it goes like this: Capital = approx. $60,000 on car depreciation over 3 year term = approx. 20%, bringing value of good to $48,000. I make payments of $1500 per mo. to my investments. Capital after first year should equal approx. $21,420. After second year, capital should equal approx $46,900. At end of third year, capital should equal approx. $77,200. That is crude, because I do not have the monthly formulae that I used to calculate interest compounded monthly on payments. But it is close. Also, I used a very basic calcuation at 19% annual growth (and also erroneously calculated the interest on the first year of capital as if all capital was invested in lump sum at begging of term, which it is not). I will see much higher growth than that on my investments however, because 50% is invested into my forex account which is currently returning approx. 80-200% annually (last year, it returned 287%, although the previous year only 97%). Over a month-long term, it is not uncommon for my forex engine to give me 1500 pips of growth (although at times it will giveback a hearty 700). Total Amount of capital expenditure: $114,000. Capital value at end of term: $125,200. Total cost of ownership for 3 years on car: -$11,200 Car will be written off also as it used primarily for work (we use my girlfriend's IS300 for personal travel). This is completely legal and totally spelled out for you on the IRS website. As is the use of deductions relating to "tools", and other expenses - such as client dinners, which are considered entertainment, I believe. Every year that I file my taxes, they are audited first by a friend of mine who is an auditor at an accounting firm, and he is very rigorous (and expensive). I have had no issues with the IRS to this point, and have contacted them specifically to clarify whether certain items can be claimed, and specifically explained how I was doing it. If I am audited by the IRS at some point, I am not too worried, because I keep receipts of everything, and to the best of my knowledge I am doing nothing illegal, have no intention to, and take every precaution in order to remain in compliance with their regulations. Most people are not aware that business expenses are business expenses, and should be counted as such. If you are using a suit primarily to conduct business, and it is a significant purchase, than you are purchasing a tool for business use and it qualifies as such. Also, Enron's accounting practices had little to do with taxes. Rather, they were grossly misstating their earnings, and filing 10q's and 10k's which were highly inaccurate. The executives and board members came under federal investigation when it became clear that they were directly involved in knowledgeably and purposefully "fudging" their earnings in order to deceive investors and influence the value of their stock, and then giving themselves massive stock grants, which they would liquidate at these falsely inflated values. This is a wholly different crime than tax evasion, or any tax code violation, and it was the SEC and the FBI who investigated, rather than the IRS.