The best question to ask while shopping

Everyone is into deals these days. I went on an email diet over Thanksgiving (definitely the only kind of diet I kept), and so I opened my In box Sunday night to find literally hundreds of offers from retailers who have somehow gotten my address over the years. I was tempted to start shopping (perhaps for some of the best deals MoneyWatch has listed at Amazon, BestBuy and elsewhere), but then I realized I haven't even started making my list yet. So, instead of looking for the best prices on items I'd already selected, I'd be shopping from the items retailers wished me to see, with the added pressure of "this weekend only" pushes.

Somehow, I don't think this would lead to sensible decisions.

Over the past few years, as I've been pondering how I should be using money wisely, I've realized that I'm incredibly swayed by sales. I'm not alone in this, of course. The entire science of retailing exists to make you believe that discounted merchandise is virtuous -- that you're somehow scoring a win when you pay a lower price than whatever the price tag (itself a somewhat randomly assigned number) says. I see the result in bags of clothes that wind up going to Goodwill, kitchen utensils we never use and food that goes bad. I think of myself as a frugal person because I shop in cheap stores and buy things on sale. But a $50 shirt that's on sale for $20, but that you never wear, is more of a waste than a $100 shirt you wear every other week.

So as I'm approaching my Christmas shopping, I'm asking myself a question: Would I pay full price for this? If I would, and I find it on sale, then I'm legitimately saving money. If not? Well, probably better to think it over, even if the sale ends Tuesday.

How do you train yourself to shop smart?