$500 for a pair of boots? You're insane and have no appreciation for the interest you could have made. If you would have bought the $30 pair of boots and thrown the other $470 into a Roth IRA invested in an index fund that tracks the S&P 5 years ago instead of buying the designer treads for $500, you would be much better off. After year one, you would have had $555 and been able to buy another pair of $30 boots, leaving you with $525. After year two, you would have had $525 (it was effectively flat that year) and bought another $30 pair, leaving you with $495. After year three, you would have had $590, and bought another $30 pair, leaving you with $560. After year four, you would have had $670 and been able to buy another $30 pair of boots, leaving you with $640. Finally, after year 5, you would have had $790 and been able to buy another $30 pair of boots. So, while you may have some worn in, designer, but out of style boots and no money, your foolish family members have $760 and some cheap, yet in-fashion $30 boots. Guess you showed them. Stop thinking of fashion as an "investment".