I have been collecting vintage clothing since my late teens. Thrifting and consignment shopping are fun and exciting. Despite all these garments, I often feel like my wardrobe is wearing me and I am hanging on to things just because they are interesting or good quality at a good price. How does one honor a love of vintage while wearing clothes that function in day-to-day life and not succumbing to style that is low-quality, unoriginal and then discarded after a season or two? — Mary, Rochester, N.Y.
I am sorry to say it, but I think the question here is not so much about thrifting as about developing and understanding a personal style. It seems as if you have gotten distracted by the dopamine hit of discovering a great item and allowed that feeling to guide your decision about the purchase without really considering whether the garment makes sense in your life.
It’s understandable. Part of the joy of thrifting is the thrill of discovery, which can’t be planned. You never know what discarded treasure you may find from what long-gone designer (or even, in some cases, from just last season). Who knows what surprising and singular item may be buried on a rail? Uncovering that kind of trophy is a thrill. Certainly more so than simply following the pack and buying yet another version of the thing that’s all over TikTok.
Thrifting is also the most sustainable approach to shopping. The longer an item is kept in circulation, the less harmful for the environment. I would never tell you to give that up.
Indeed, I wish more people would engage with the secondhand market, rather than ultrafast fashion. But it sounds as if, in your thrifting excursions, you are prioritizing more outré items over, say, classic ones — perhaps because they seem more special.
As Hamish Bowles, one of the foremost vintage collectors I know, pointed out when I asked, it is possible to find a pair of great black pants or a trench coat in a thrift store. You just can’t necessarily plan on it.
It is also true that sometimes those rare items that looked so great in the store can look like costumes in real life. (Sometimes, that’s the reason they ended up in the thrift store in the first place.)
This matters when you consider the messages your clothes are sending to those around you: Do you want them to think you are eccentric? Artsy? Focused? Or, perhaps, pulled together with a touch of creativity, which sounds like the image you are after. In which case the answer is not to abandon the wardrobe you have built, or the satisfaction you once found in it, but to make it serve you.
To do that, you need to start with a foundation of neutral classics like tailored black pants, a great button-up white shirt, a cashmere crew neck, a thick white cotton tee, a navy blazer. These are pieces worth investing in when it comes to fabric and manufacturing. Think of them as the basic canvas onto which you can layer your thrift shop finds.
A wild print skirt with or without embellishment becomes a focal point, not a distraction, when paired with a white shirt. Ditto a bejeweled shirt married to some plain trousers. The goal should be balance, in fashion as in life.
And what that means with respect to your thrifted finds is being more discerning.
“Many of my friends follow the ‘one in, one out’ rule,” said Cameron Silver, a luxury brand consultant and the founder of Decades, one of the original high-end vintage stores, who also advises clients on closet organization. In other words, for every vintage piece you add, choose one to relinquish.
“I’ve spent the past few years selling much of my own wardrobe at auction and found it incredibly liberating,” Silver said.
You should not feel bad about de-accessioning anything that doesn’t pair well with a more timeless piece. “Clothing is constantly circulating through the resale carousel,” Silver said. “So reselling something that was previously purchased secondhand is hardly an issue.”
The point is, you aren’t breaking up with thrifting. You are simply changing your rules of engagement.
Your Style Questions, Answered
Every week Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or X. Questions are edited and condensed.
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