The Nerd’s Guide to Thrifting

I’ve been a ‘serious thrifter’ for the better part of two decades (holy cow, that makes me feel old!) ever since I discovered our local Salvation Army and Goodwill stores in the little Michigan town where I spent most of my childhood. I still remember the time I came home with a huge bag of lovely dress clothes for my first high school internship at an art gallery. I felt like a princess, like a whole world had opened up to me on my minimum-wage, weekly-allowance, gas money existence! Since then, I’ve learned a thing or two (and made a few mistakes… Ok, make that a lot of mistakes…) and I’m hoping that through my own experiences, and my passion for psychology and economics, I will be able to add something new to the practice of thrift shopping and that it will be of help in some way!

I’ve released this series in six parts on the blog, but I also wanted to offer it in its entirety in case the intrepid reader might like to take it in all at once! Thanks for reading, and I hope you enjoy it!

1. Try to maintain a broad perspective.

Especially when you’re not at thrift stores known for their high quality, it’s very easy to find one mediocre piece amongst the dull and low-quality options and accidentally only see it in comparison to its sadder compatriots. This is analogous to the idea proposed by psychologist Daniel Kahneman called ‘narrow framing,’ which is the tendency for investors to be too myopic when they consider specific investments, forgetting to keep a broader perspective of their entire portfolio in mind. (It’s also just a general cognitive quirk that we are really good about comparing things that are right in front of us, to the exclusion of the rest of the world! This once-adaptive human ability is now much more difficult to manage in such a complicated modern environment, resulting in systematic errors, or ‘biases.’)

I made this mistake for years, oddly not discovering my error until I moved from New Mexico to Seattle. Largely due to this kind of error, it was really hard to see that I rarely ended up loving anything I bought at thrift stores in Albuquerque because they just didn’t have much retail that was my style in the city (see point #3).

How to deal with it:

  • Imagine how your closet looks at home, and then imagine hanging up the new piece alongside your other carefully-selected favorites. If it dulls in comparison, put it back and get outta there!
  • Imagine you’re at the mall or shopping online for something new. Does the item in question compare to what you might’ve found new in a store filled with lovely options and all manner of sizes to provide the perfect fit? Or is it just the best thing you’ve found on that particular thrifting adventure?
  • Along the same lines as the last point, try to guard against ‘thrift store good’ versus ‘bought new good’ mental categories. All the items in your closet should be on the same level in terms of joy, quality, versatility, fit, or whatever categories you value. Unless you’re there to buy some clothes to get paint on while you refresh your living room, you should train yourself to always compare every new purchase with what you already own, regardless of where it came from or how good of a deal it was. This is analogous to the cognitive error we make with money where we religiously clip coupons for .50 cents off a $3 loaf of bread, but won’t drive across town for $100 off a $20k new car purchase from a different dealership running a sale on the same car. Our tendency to reference the wrong items for comparisons–the clothes around us in the thrift store, or the large $20k pricetag–creates mental categories that turn out to be totally arbitrary. The $100 doesn’t know where or how or why it was saved, it’s just $100 still sitting in your bank account. Likewise, that ‘thrift store good’ skirt ultimately may just be a mediocre skirt hanging in your closet.

2. Be willing to leave with nothing.

This applies to shopping in general, but it’s especially problematic in thrifting. Often times if we spend a lunch break or a long weekend afternoon of our precious free time sorting through endless racks of less-than-stellar finds, it can be very tempting to convince ourselves that we really should leave with something to show for our efforts. But if you don’t catch yourself before the checkout lane, you’ll end up bringing home something that you don’t end up wearing–which is kind of the point of the whole thing.

This is especially problematic when you have very limited free time (hello to myself just after I had each of my babies and could only leave the house solo for an hour or two every week–at most!). This is such a problem because of the idea of ‘preciousness.’ This is a specific application of the basic idea of limited resources and all the crazy things we do when we feel trapped, controlled, ‘rationed,’ or otherwise locked out of things we love and value, but suddenly find ourselves with a small amount of said limited resource.

I first heard the term ‘preciousness’ in an article years ago by the artist Stephanie Pui-Mun Law where she talks about errors novice artists tend to make with their time and their art materials. She says that when artists find themselves faced with large amounts of time to do their work, especially if this is an infrequent experience for them, they often find themselves paralyzed and unable to work because there’s no way they can ‘make it count’ or live up to their own expectations to paint that masterpiece ‘if only they had the time.’

It sounds ridiculous to apply that level of thought to something so trivial as thrift shopping, but it’s really the same thing: Say you work fifty hours a week and your free time is extremely rare, and you really want to go shopping (this applies to pretty much any type of shopping, or leisure activity in general). You go in so excited about the possibilities, but after a while, it becomes increasingly possible you may not find anything great this time. Maybe you’ve got a few OK items in your cart, but you weren’t that thrilled about them when you first pulled them off the rack and tried them on. But now that it’s getting time to leave, those ‘meh’ items are starting to look better and better, and you’re starting to construct justifications for why they might actually be better than you thought.

That’s a problem.

And on top of that, there’s the whole realm of hormones and neurochemicals and blood sugar levels and cognitive fatigue–basically, if you shop for hours without eating, make a long succession of decisions about what to buy, and are extra vigilant for those unicorn pieces that you could easily miss if you mentally ‘check out’ for two seconds, your brain is just not going to be as bright-eyed and bushy-tailed as it was when you walked in.

By the time your stomach is growling and your partner is texting you angry emoticons from home, or–even worse–you’re on the clock and need to hurry to get to your next engagement, you’re ripe to make some less-than-optimal decisions about what to buy. That’s the time when the ‘it’s just $2’ sounds like a really good plan, or when you fall back on the ol’ Thrifter’s Curse of ‘I’m not sure, so I might as well just get it so I don’t regret leaving it behind later.’

How to deal with it:

  • Be willing to live with a few regrets. We generally regret a lot less than we think we will, and the decisions we make to avoid regret tend to not be very high quality. (And take it from me, most of the times I’ve panicked and regretted not getting something, it was still there when I went back the next day. When we really want something, we tend to think everyone else feels the same as we do–and thus someone will surely scoop up our great find before we can make it back there!–but I’d say at least 80% of the time, it’s still there just waiting for me when I’m more sure of my decision, which is a much higher quality decision after I had more time to think about it.)
  • Humans waste a good deal of resources in order to ‘keep our options open.’ You need to be willing to be ruthlessly picky about your own sense of style (once you’ve found it, that is–’exploration phases’ don’t quite follow these same rules) and thus willing to risk regret to fiercely protect all the hard work you put in to decluttering your closet, or building that perfect capsule, or staying within a fixed budget, or whatever it is that motivates you and makes you want to be more principled in your purchases.
  • This is a very important point that pertains to mental health–if you are skimming through all my tedious explanations, you may want to slow down for a second and read this bullet point carefully. If you need that precious free time to be a stress reliever for you, you need to ask yourself a very important question: If I found nothing at the store today, would I still feel I got the de-stressing I needed? Is just perusing and trying things on and daydreaming enough for me to feel joyful or relaxed? Or might I leave empty-handed and feel like I should have spent that time with my family, or that I would have been better off reading or taking a walk in the woods? I will go deeper into this in other posts, but it’s part of a larger picture of what we usually think of as long-term versus short-term happiness. If your time is that precious and you know you might not get what you need for your mental health if you don’t get that wonderful neurochemical reward from finding something really great, don’t go. It’s very much easier said than done, but at least take the first step towards healthier habits by being honest with yourself, if you’re starting to rely on that burst of reward that may not come. Shopping is obviously addictive for many reasons, but thrift shopping in particular is very addictive because there’s always that small chance to stumble upon that unicorn find, and the more you show up and shop, the greater those chances are. You can’t control when it happens except to keep showing up. If this feels relevant to you, stay tuned, because I will go into this a lot more soon in a post about shopping addiction, a topic that is near and dear to my heart for many reasons.

3. Try to thrift in regions or cities that have retail stores that you like.

Simply put, if you don’t live anywhere near a mall that has a J. Crew and it’s is your favorite brand, you’re going to be hard-pressed to find much J. Crew at your local Goodwill. Yes, people do order online more these days, but–I lack the data to back my conviction here, but you can test it for yourself if you haven’t already!–the probability of finding brands at thrift stores that aren’t sold locally seems to be relatively low, especially if they’re obscure, small, or new brands. Also keep in mind that if your style doesn’t generally fit with the style of your chosen area of residence, you’re also less likely to find pieces you’ll love (for example, living in the Southwest for five years surrounded by bolo ties, shabby chic, and bright pops of Mexican color, while certainly beautiful, just wasn’t for me).

How to deal with it:

  • Obviously, you can make pilgrimages to big cities with better retail options–and thus better thrifting–or make time during vacations to sneak in some thrifting in world-class destinations.
  • Try out some online consignment. I am a longtime ThredUP user–I have lots of experience with both buying and selling–and though I’m not 100% in love with every aspect of ThredUP, I think they are by far the easiest and simplest online consignment option, and they seem committed to making continual improvements to their platform, services, and offerings. I can’t speak as much to the other options such as Ebay and Poshmark, but I have purchased from them a few times with generally good results.
  • If you don’t like or have access to either of these options, you’ve probably already found retail brands you like. Ultimately, what we’re looking for is a closet full of clothes we will love and wear for as long as they fit or fall apart. If you’ve been thrifting for a long time and just don’t ever seem to have much success, especially if you’re caught up in the churn of thrifting items one week, only to donate them back soon after (I call this ‘renting,’ and it’s not always a bad thing–I have an article about that in the works that I’ll be posting soon!) then maybe it’s time to admit that thrifting just isn’t your best path to a wardrobe that makes you happy.

4. Avoid the ‘almost perfect error’

I’m sure we all could share at least a few memories of finding pieces that were so tempting but just slightly imperfect (pin holes, stains that just might wash out, missing buttons, frayed or too-long hemlines). If you’re an avid sewist, or if you already have a reliable tailor or dry cleaner that you frequent, I say go for it. But if your sewing machine has been gathering dust in the basement, or if you haven’t yet found a good tailor or cobbler in your area, the piece may just find its way right back to the thrift shop after sitting folded on your closet floor for an embarrassingly long time (ask me how I know…).

How to deal with it:

  • Do the math: This is related to point #1, where we get so excited that we found something great that we forget to do the simple mental math about the total cost of the piece post-alterations, cleaning, cobblers, or expensive shoe inserts (don’t forget to include your time in these calculations–time is one of your most valuable resources!). Sometimes just that alone will help you see it’s not quite the deal that $4 price tag makes it seem.
  • After doing the math, compare the total cost to the price of a new piece. This is a stickier proposition, because from a sustainability perspective, it’s always better to choose secondhand. But if the total cost comes close to or exceeds the cost of a new piece, you have a few options: If the brand is not particularly ethical, you could just go for the mend. Or, you could try to find an ethical brand that carries a similar product that better deserves your hard-earned money. But ultimately, this is a personal decision, and if it’s a piece that you will wear often, it’s still of reasonable quality that should stand the test of time, and you have very limited time or money, it’s not always easy to steer clear of questionable ethics (I talk more about that in this article), and the best choice might be to purchase new.
  • If you’re the kind of person that already has a proven track record of mending your clothes or generally just getting things done right away–and you do the math and it still looks like a good deal–go for it! But if you’re like *ahem*…me… and your ‘to-mend’ pile languishes for years with the price tags still attached, eventually graduating from the ‘to-mend’ pile to the donate pile, try and be realistic. If you can’t wear it and you don’t think you’ll get to dealing with it anytime soon, it’s just not worth it.

5. Avoid the allure of the ‘good-enough great deal.’  

This has been said many times by others, but it bears mentioning again because it’s so easily forgotton: No matter how cheap something is, it is never a ‘good deal’ if it’s not a piece you’ll actually wear. Usually this is a point made about fast fashion, but it’s also a major source of errors in thrifting, because there’s a good chance of finding great deals when the price points are always lower than retail. Great price points have a way of beckoning us: ‘Just try this out, maybe it will be the best article of clothing you own!’ Even when we know we should know better, sometimes it’s too easy to just say, ‘It’s only $2, I can just donate it back if I don’t like it!’

How to avoid this:

  • Keep a list of items you already know you want, and resist the temptation to justify the addition of new items on the spur of the moment at the store. If it wasn’t on your list when you walked in, at least do yourself the respect of honestly acknowledging it is an impulse purchase, and decide if it’s still a reasonable purchase in light of the truth.
  • If something just seems good enough but not great, I like to imagine that when I leave it behind, someone comes in later that finds it and is actually, for-real excited about it, and they know it’s something they will wear a lot and cherish forever. It may not actually go down like that, but hey, how would I know?!
  • When you find yourself uttering the phrase, ‘It’s only blah-blah dollars,’ red flags should go up! That probably means you’re justifying it purely on the basis that it’s cheap. This is a really hard one to overcome because your brain actually starts to distort and justify weird things when it thinks of something as a good deal, so don’t beat yourself up if this error is a particularly ‘sticky’ one to get rid of.
  • There’s a lot of research about how price points mess with us in general (there’s been more than one study conducted about wine tasting that really drives this point home). The best thing you can do is to practice being more aware and honest about how prices might sway you to think something is more or less good than it is in reality. It’s a skill that takes time, but your closet and your wallet will undoubtedly reward your efforts!

6. Initial excitement is not actually always a true indicator of a good piece.

This is a tricky concept to unpack, and it can manifest in a lot of different ways with varied results. I can’t tell you how many times I’ve found something and lost my mind with excitement, only to bring it home and never wear it–in fact, even just a few weeks ago, I found a pair of shoes that I was just elated to have found, only to get them home and immediately wonder what in the seven kingdoms was I thinking?! First off, don’t beat yourself up: Getting familiar with return and exchange policies is your first line of defense. If that isn’t an option because the tags are off and it’s already in the wash, or in rotation but it’s just not working out, try consigning it or selling it. And if that doesn’t work, the obvious next step is to donate or gift it to someone who might really appreciate the item.

Ultimately, the point is still just don’t beat yourself up about it. If fashion exploration is your passion, then finding out what doesn’t work is as valuable–or arguably more valuable–than finding out what does. And give yourself some credit, too: You bought it secondhand, which means you didn’t put another article of new clothing into the churn, and you probably didn’t spend retail prices on it. Don’t forget that!

The harder part to tackle is the question of why we make these mistakes. Often it is the narrow perspective issue we looked at in #1; it seemed so great in contrast to what was there, but not so great in contrast to what you actually own. Or it could be issue #5, where the excitement was more about the great pricetag than the actual item itself.

How to deal with it:

  • As I’ve already said, return/exchange, consign/sell, or donate/gift the item, and practice the art of not crying over counterfactuals (‘coulda/woulda/shoulda’) and sunk costs (money that’s already been irreversibly spent). It’s not always the best thing to tell someone to ‘think like an economist,’ but in the case of sunk costs, the best course of action is to just move foward with the situation as-is without ruminating over what could have been. And hey, if you can practice this with a bad $5 vintage poodle skirt purchase, you’ll be in much better shape to handle those unfortunate-but-unavoidable bigger future purchases you might someday regret! Of couse, do your best to avoid making the mistakes in the first place (more on that later!), but in the event of the occasional mistake, it’s best to just move on and forgive yourself.

7. Don’t leave your final decisions for the last minute.

This point has come up in other parts in the series, but it deserves its own section in further detail. There are two optimal times to make a decision about whether to purchase something, and neither are in the checkout line while you’re running late to your bestie lunch date.

1. The first optimal time is very soon after you pick something off the rack. Yes, of course, always try it on before you buy! But this is the first test that a potential purchase has to pass; deciding whether something is worth carrying around for the next two hours and trying on should mean that, if it fits right, it’s probably a go.

If that sounds weird, there’s a good reason why I’m suggesting making a fairly clear decision at that point: The times when you’re very first picking out items are more likely to be earlier on in your thrifting adventure. It’s certainly going to be earlier than the checkout lane (last-second ‘holy crap I can’t believe I missed that!’ finds notwithstanding), which means you’re (hopefully) more likely to be in a good decision-making state and less likely to be hungry or physically or mentally fatigued.

2. The second optimal time to make a decision is while you’re trying it on. In fact, this is really the best time.

(Pro tip: Don’t look at the mirror until after you put everything on and get it situated properly. If you stand there tugging at things while looking at it, you’ll miss the opportunity for the ‘big reveal,’ which is a great moment to experience those first, uncensored thoughts about how something really looks on you. Especially if you’ve already fallen in love with it, that moment when you finally see it on can either be the home run or the ‘wow, did I get that wrong!’ moment, which is an invaluable diagnostic.)

It’s not always that easy, though. A lot of the time, I find myself unsure about something, and unfortunately the try-on doesn’t always clear it up. But in 90% of those cases, the fact that I’m unsure is its own red flag to go back to part 1 and imagine how it would fit in with everything I already own. Chances are, it won’t pass that test if I’m still ambivalent about it even after trying it on. In those cases, even if it triggers that ‘regret fear,’ do the brave thing and hang it up on the go-backs rack.

How to deal with it:

  • Spend the bulk of your ‘deliberation time’ when you first pull it off the rack and in the dressing room. Consider the moment that you step out of the dressing room as the time for final decisions, not just before you check out.
  • If you catch yourself throwing every single ‘meh’ sweater into your cart, stop–eventually you’re going to have to make some decisions, so don’t let your brain get lazy and assume the decision will be easier later. (It won’t.) The one exception here is if you really do love something, but you’re not sure how it will fit. It’s perfectly fine to be on the fence about something until you decide if you like how it fits. What’s not so great is having a cartful of stuff you just threw in on a whim that you’re eventually going to have to deal with, because if you leave that kind of pile until the last minute… Well, that’s most likely going to yield some pretty crappy decisions.
  • Don’t try everything on at once. Stop periodically when you’ve got maybe 4-8 items at most, so that you can have time to think. Don’t wait until you’re running late with a cartload to trip in and out of fifteen different pairs of yoga pants–you’d have been better off just picking out 5 at a time and trying them on, even if you don’t make it through every section you had initially planned to look through. It’s better to make good decisions about a few items than bad decisions about fifty–and it’s better to leave with one great find that you feel confident about than ten you just grabbed because you didn’t have time to think each one through.
  • Carry your clothes in your arms instead of a cart. Yes, I know this sounds ridiculous, but it will make you much more discerning in what’s worth adding to your load. If you opt for a cart, at least keep a mental note of how many items you’re allowed to take in to the dressing room at one time. Especially if they’re like most overcrowded thrift stores here in Seattle, during the busiest times, you’ll only be able to try on maybe 5-6 items at once before you have to go to the back of the line and start all over again. If you’ve just grabbed everything that looked vaguely interesting without taking the time when you first pulled it off the rack to think for a second, you’re probably going to regret putting off any decisions if you have to go back through a line multiple times. When I do grab one of those wheely cart-basket things (I probably found a heavy ceramic plant pot, because I am also hopelessly houseplant-obsessed) I almost never let myself put more items in the cart than I can take in the dressing room with me at one time. When I hit that limit, I go try on everything, and then go back to shopping if I wasn’t done yet.

If you enjoyed this post and want to delve further into any of these topics, here is my list of books and other media that you might want to check out!