As I was prowling the post-holiday sales at my local shopping mall, I got to thinking about shopping strategies. A common piece of wardrobe-building advice – regularly offered in fashion magazines – is to invest more money in “classics” – like a crisp, white dress shirt or black slacks – and then save money by purchasing cheaper versions of trendy items.

I’m going to flout the fashion pundits and confess, on record, that this approach has never worked for me. It ignores some basic realities. First, any item of clothing has a finite lifecycle. Fitted shirts develop armpit stains, sweaters become scraggly, and things stretch or shrink and slowly lose their shape. Second, everything slowly slides out of style. Although in theory this process happens more quickly for trendy items, and less quickly for “classic” items, I have found conventional wisdom about their lifecycle differences much exaggerated. Black pants, per se, may not go out of style, but the shape and cut of any individual pair of pants most certainly will. Conversely, something that was on display in stores everywhere last year is unlikely to make the wearer feel uncomfortably out-of-sync this year. In short, I haven’t found that the usual suspects on lists of “classic” items necessarily lasted longer and were more worthwhile expenditures than “on trend” items.

So, how to know whether that divine, pink trench coat is worth the price tag? Cost-per-use. If you were to divide the cost of the item by the total number of times you imagine you’ll wear it, what will it have cost you to wear each time? Items with a lower cost-per-use are a better use of your money – even if the initial price tag is higher.

Some key characteristics to identify a low cost-per-use item, even if the initial price tag isn’t low:

1. You like the way you look wearing it. (You won’t wear it if you don’t feel good in it.)

2. The item coordinates well with other clothes and accessories in your wardrobe.

3. The item fits with your lifestyle. You can immediately think of places you’d wear it.

4. The item can sustain regular use. I’ve found that fitted shirts – which develop armpit stains at the speed of light – almost never can. For me, fitted shirts aren’t worth a lot of money.

5. The item is a *regular* use kind of item. Many people splurge on special occasion clothes and save on daily wear; I’d actually recommend the opposite. Wouldn’t you like to wear beautiful, special things every day? Conveniently, that’s how you can make a splurge price worthwhile!

6. You love it, and want to use it regularly!

Only you can say whether a new potential acquisition meets these criteria. But if that pink trench flatters you like a lover, could comfortably become a go-to jacket in the spring and fall, and would last for a couple of years, then it may very well be worth the cost. May this simple, pragmatic approach help you create a flattering, fun, economically-sound wardrobe you love!