1. What will this go with from my current wardrobe?
Try to come up with at least three outfits you could see the potential purchase working with. Teamwork makes an outfit. If you don’t have anything in your current lineup that’ll play well with the potential new addition, then it might not be the best buy.
2. Where will I wear this? Can I think of three circumstances in which I’d wear it?
That madras jacket might be smokin’… but where are you going to wear it? Would you really wear it to happy hour with your pals to watch the game? To work? At home on a lazy Friday night? If you can’t picture more than one place or one event you’d wear it, weigh that limited use against the cost.
3. What’s the return policy?
Is it a final sale item? Are you on the hook for return shipping? Are there free in-store returns? Is there a very small window for returns? It gets more complicated with online purchases, but it’s still good to know.
4. Do I already own something similar?
Let’s say there’s this hypothetical person who may or may not own five navy blazers (wool, corduroy, rumpled cotton, chino, and linen) with… hypothetically… a potential sixth on the way (tweedy English wool). This hypothetical person could have saved himself a boatload of money if he would have learned to ask himself this question earlier. Hypothetically.
Pretty sure we’re set on navy sportcoats & blazers here.
5. Do I even like wearing this style/color/type of thing?
Plenty of us often purchase articles of clothing that we’ll hardly make use of. Personally, I don’t wear sneakers that often. But recently I found myself drooling over a pair of rich-suede sneaks from Tretorn. Right before I clicked “complete order”, I saw the three pairs of classic sneakers I hardly ever wear sitting in the corner collecting dust. Purchase averted. Just because something is aesthetically awesome, and a great buy, doesn’t mean you’ll actually wear it.
6. Will this soon be out of season?
Buying during end-of-season clearance sales is a great way to save money. But what if you’ve got a few wants/needs for the upcoming season? Balance.
7. Is this a trend that’s going to die off soon?
Worst case scenario: Buying something that soon goes out of season and is at the tail end of a trend.
8. Are there additional costs like tailoring, storage, and/or maintenance?
It rarely ends with the price at the register .
9. Would I buy this if I was sober?
Drunk, late-night, online shopping is a real thing.
10. Is the main motivator for buying it the sale price, not the style?
Drunk on discounts!
11. Will I be too scared to wear this?
This is a real thing. You invest in a suit or a watch or a pair of shoes and… it just sits in your closet. You never wear your “good” stuff because you’re afraid you’re going to spill something on it, get it scuffed up, etc. Don’t be.
Of course, these are all questions that are asked AFTER the big important ones: Am I living paycheck to paycheck? How’s my emergency fund? What about retirement? Y’know, that kinda stuff. Super fun stuff.