Will I still want to wear it in 10 years?
No one can be absolutely sure of this answer, of course, but sticking with classic styles for you will place the odds in your favor. I've had a few constants, like Birkenstocks, overalls, and long-sleeve jersey tees that I've incorporated into my style for more than a decade--replacing items as they get worn out. With these, I hardly have to ask myself to know the answer to this question. Knowing my foundational pieces, the anchor to my style, helps in knowing whether spending more on something might be worthwhile.
For me, part of the problem lies in the fact that my foundational items are not the sort that I need to spend a lot on, which may not seem like a bad thing except that it makes my whole wardrobe disposable. And these items work best for a casual life that I have half outgrown. Birkenstocks top out at around $100, and jersey tees soon get stained and worn out. Overalls look best the closer they are tied to their functional roots. So for me, the dilemma lies in knowing what could work as anchors of a more elegant and grown-up style, one that I'd like to move towards.
(Minor sidenote: A few years ago, I wasn't concerned with this question at all. My thinking was that I should indulge in the items that I wouldn't be wearing in a few years, and wear them while I still could and wanted to. Hence, I now have many impulsive purchases to be gotten rid of, but I don't exactly regret those purchases. They fulfilled the purpose I had for them at the time, and they gave me a lot of pleasure.)
Does it fit my lifestyle?
Fashion is all about aspirational thinking, which I think confuses the issue. You see pictures that provoke desire but have no correlation to your own life. It's easy to forget. And it's a fine line, when dressing is tied so closely to creating your identity, and sometimes you dress for who you'd like to be, rather than who you are at exactly that time.
I don't have fancy parties to go to, but I still thought I might get a lot of wear from the Rachel Comey Blithe tee I blogged about yesterday. I thought I might enjoy the incongruity of wearing something slightly formal as an everyday piece. But then I pictured myself in my day-to-day life and saw that a semi-sheer, oversized silk tee would inevitably tug downwards, become stained, and be relegated to a back drawer. So I packed it into a box to go back.
Is it weather appropriate for where I live, and how much out of the year will I wear it?
I'm still having to remind myself not to spend a lot of money on warm-weather clothes. Even now, out of habit, I want to buy pretty dresses and short-sleeve tops, but I know my money is better spent on cold-weather clothes that I'll be wearing most of the year. This question prompts you to think of the cost-per-wear of the item.
Do I have several like it already?
This one is a bit tricky. I think it's fine to have multiples of your foundational pieces. In fact, I'd love to have a uniform where all the pieces in my wardrobe are simply variations on a theme. But sometimes having many of the same thing means that none of them are exactly right, and it's time to stop and analyze what I'm really looking for. Too, I don't like to have items that are too similar or differ only by color because invariably there will be one version that I prefer and wear to the exclusion of the other.
There are other questions that factor into the equation--like, how much do I love it, and is it worth the price asked--but these were the four questions that kept popping up into my head as I was sifting through my choices on that sleepless night. I'll be keeping them in mind the next time I want to buy something.