Be a financially savvy shopaholic
(Note: The shirts in the photo are hideous. People who use my theory to justify buying ugly clothing will be prosecuted to the fullest extent of the law.)
I confess. I am a shopaholic. I go shopping for clothing at least once per week. I have four pairs of Puma's, eleven track jackets, eight sweatshirts, and way too many t-shirts. My friends don't understand. "You write about investing and personal finance. You pick up pennies on the sidewalk, save more money than any of us, and are one of the only people I know who actually knows the interest rate you receive on your savings account. How can you shop so much and yet claim to be financially literate and responsible. Zac, you hypocrite."
I have never really bothered to explain this to anyone, but I actually have an elaborate theory that explains why my frequent shopping and large clothing collection is not only permissible, but even responsible. The theory is called Zac's Law of Diminishing Usage. It goes like this: The more clothing you have, the less you will use each piece, and therefore the longer each piece will last. With items that are not subject to going out of style, the marginal cost of each additional piece is 0. Shop til you drop!
While I do shop frequently, I only buy at stores like Marshall's and TJMaxx and Filene's Basement. Furthermore, I only buy stuff off the clearance rack, and I only buy stuff that I consider to be timeless: Puma shoes will always be cool as will jeans, and I will always wear track jackets. Yesterday for example, I bought a Quicksilver t-shirt for 2 dollars, a pair of Calvin Klein jeans for seven, and a pair of nice but non-name brand shoes for 6 dollars. I also bought a pair of Seven jeans for 20 dollars (premium denim..almost as nice as True Religion's).
Here's why it works: If one pair of shoes lasts six months worn every day, 10 pairs worn once every 10 days will last 5 years. Furthermore by being selective and limiting yourself to buying clothes you love that are available at a great price, you may actually save money. You will no longer feel the pressure of needing new clothes now and having to pay retail price. There may be some loss due to the time value of money (Investing cash now and then buying the clothing later may leave you with better purchasing power.), but the effect is likely to be minimal.
Caveat Emptor (Wow, my four years of studying Latin finally came in handy.): Because you may accumulate a larger wardrobe than you presently have and will be wearing clothes less, the clothing will last longer. Only use this theory to stock up on perennial favorites that you see yourself wearing a few years down the road. Anyone buying 11 pairs of Crocs does not have my blessing. Also, if you do not enjoy shopping, you may be better off just paying retail and doing it all at once. Nothing is as valuable as your time.
So there you have it: Zac's Law of Diminishing Usage. If you enjoy shopping and bargain hunting, feel free to buy as much clothing as you like!
Some sites of interest to get you started bargain-shopping online, if that appeals to you:
Overstock.com: Use the site, don't touch the stock.
BlueFly: This is more expensive, designer clothing, but it's a good deal as that stuff goes.