Source: Stylizimo

I had naively thought, right after I graduated from college, that I could continue to get by on the two suits–one skirt-suit and one pantsuit–that I wore on repeat for summer jobs. That plan quickly crumbled as I grew bored and increasingly desperate for variety.

My blog was born out of that desperation: it was both an outlet to channel my latent consumerist tendencies, and also a platform on which I built friendships (many of which eventually went offline and became beyond fashion) with members of the burgeoning petite fashion blogging community, who made the process of building an adult wardrobe less lonely.

As with any learning process, it’s full of avoidable mistakes. And wardrobes are meant to evolve with their owners, so there are multiple turning points at which massive purges are necessary. Longtime readers of this blog know that I used to collect cocktail dresses with fervor, and they were useful in my mid-20s as I rarely had to scramble to shop for weddings or special occasions. But as wedding invitations turn to birth announcements, I have had to re-home many cocktail dresses.

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To start, purchase regrets are not a personal failure. Everyone makes them; they are inevitable. Some trends (and more broadly, decisions) just don’t age well, you know? That is why I try really hard to abstain from “investing” heavily in a trend before I can grasp its holding power. It’s much less painful to part with one mistake than 10 mistakes.

Speaking of 10 mistakes–and this is an instance of do-as-I-say-not-as-I-do–unless you shop once in a blue moon, you don’t need 10 t-shirts in the same color or 10 pairs of cognac boots. If you can play by this one rule, you have already avoided 31.528% of regretful purchases.

And then there’s the I-Should’ve-Just-Bought-the-Original-Thing-Instead regret (or its cousins I-saw-something-similar-on-a-chic-person-and-scoured-the-web-for-a-lookalike-that-I-never-wore and I-couldn’t-possibly spend-500-dollars-on-this-top-so-I-will-just-buy-10-tops-that-I-feel-lukewarm-about-at-50-dollars-each-and-will-eventually-donate-them-all). Who among us hasn’t opted for the “look-for-less” option? And sometimes those purchase sate a craving, perhaps long enough for the craving to pass. But for me, most of the time the only purchase that will do is the prohibitively expensive, past-season, impossible-to-find-in-your-size option. If you are an optimist like me, you can postpone that purchase by saving that search on eBay and then eventually–maybe one day–forgetting all about it.

Also problematic are aspirational purchases. Be it buying something in your aspirational size, or buying a special occasion piece for an aspirational event. I am not advising against these purchases because I don’t believe in you, I just know that, when the time comes, you will probably make different choices than the ones you make today.

Lastly, and this is a problem I worked on intentionally because it is my downfall: the sale-induced delirium. I am a sucker for good deals, and used to shop final sale and buy things sight unseen (the horror). I would guesstimate that 95% of those purchases ended up living very short lives in my closet and are donated within a year or so.

To summarize, here are the conditions under which I am likely to regret a purchase: when they are redundant; when I buy something on a fire sale; and when I allow the idea of something to overtake the practicality of the thing.

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So apply what you know about yourself to write the rules that will filter purchases that are highly probable of proving regretful, in addition to these handy lessons that I have learned.

  1. Spend on what’s practical. I don’t ever regret the dozen or so pairs of running shoes that I own, because I enjoy running and I wear them all, if not every day. I’ve only regretted buying running shoes when I get caught up in the style and settled for a poor fit. In the same vein, I don’t regret spending more on workwear, because they are less trendy, and I don’t foresee myself making career changes in the near future that would necessitate a brand new work wardrobe. As what’s practical for me may not be practical for you, you alone can assess (and be honest with yourself here) what’s practical. But I have never met anyone who’s regretted spending more for things that they use often. (Exceptions here.)
  2. Avoid retailers with draconian return policies, and shop final sale sparingly. Final sale is not a four-letter word, but you should avoid them at all cost when you are unfamiliar–that is in any respects, be it fit, quality, etc.–with the retailer in question. And if you are someone whose life does not allow for timely or easy returns, you may need to reconsider the channels through which you shop. Even someone like me–who lives life at a languid pace, has access to a car, and passes by both a post office and an UPS on my way to work–can occasionally fail to return purchases within a 30- or 60-day window.
  3. Return even lukewarm purchases. Few people on their deathbed are wondering about that dress they mistakenly returned. I am not a Mark Manson fan, but his Fuck Yes or No philosophy applies well to shopping.

And should you ever transgress any of these rules, take swift action: gift or donate or sell, because space is precious.

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Lastly, because the person who inspired this post asked specifically about my biggest purchase regrets, a (short and generic) list of things that I regret buying and have since parted with:

  1. 90% of cocktail dresses that I at one time or another loved and may have spent an inordinate amount of energy trying to find or buy on sale. I should not be surprised by my own fickleness, but I often am. I suppose a bigger lesson to be gleaned from this is… if you don’t have an occasion for it, you probably shouldn’t own it. But I do believe in trophy pieces: the difference here is you find occasions for trophy pieces that you wouldn’t for merely impractical ones.
  2. As I mentioned earlier, most of the things that I buy on final sale sight unseen. There are just so many ways for the purchase to go wrong, especially when it comes to fit.
  3. Duplicates. For example, while I wear striped shirts a lot, I own way more than is necessary. Just because something is to my taste does not mean it belongs in my closet.
  4. Things of poor quality–be it material or workmanship. Sure, I might not have spent much money on it, but when would I ever choose to wear that exceeding itchy acrylic-blend sweater?
  5. Children’s clothes. While I may never stop shopping Zara’s kids section, I now have enough awareness to scrutinize every potential purchase carefully. One day I hope to just outright refuse to consider a purchase from the kids section.

What are some purchases (or other decisions) that you’ve regretted? Write me!

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