The vintage T-shirt sector — especially the vintage concert T-shirt sector — has become an increasingly rarefied collecting space, one that inspires the same level of connoisseurship, obsession and knowledge as any decorative art. Often such T-shirts exist in extremely limited numbers (and sizes), have their own graphic value and represent a specific moment in culture and politics.

In a world where it often seems as if fashion has become generic and every garment is the same everywhere, vintage tees have a different kind of allure. I think of it as the three S’s: singular, special and sustainable. Taken at face value, they mostly just look cool, but for those who recognize the provenance, they act like a secret password: Those who know, know.

That’s why, for example, a 1967 Grateful Dead shirt sold at a Sotheby’s auction in 2021 for $17,640. It’s why sites like WyCo Vintage (where you can search the offering by year, color, band and measurements) and Ellie Mae Studios (where a 1990s Nirvana Nevermind tour shirt is currently on sale for $890) get traded like secrets.

And it’s why the question of whether you can wear such a garment to work is more complicated than just: Should you wear a T-shirt to the office? It’s also about how much of your private passion you want to share in a professional space.

On the one hand, being able to bring your full self to work, including your most serious hobbies, is satisfying and often restorative. Also, such personal details can double as a talking point and icebreaker in any meeting.

On the other hand, they are also revealing, and you will have to deal with any preconceptions someone who may not know you well will bring to the table if, say, you suddenly appear in an Iron Maiden T-shirt (highly covetable as that may be). And some professions — law, finance — obviously tend more than others to the generic suit philosophy, where personality is subsumed to institution.

Increasingly, however, such dress codes are flattening out, which means there is more wiggle room no matter what job you have. That means that the best approach to sartorial collectibles like concert tees may be to introduce such wardrobe elements strategically. (Note that this is true no matter what your gender.)

Jon Caramanica and Jacob Bernstein, colleagues and T-shirt connoisseurs, suggested pairing the T-shirt with a cardigan and a pair of well-cut trousers. According to Mr. Caramanica, “It’s an approach that allows you to show just a slim segment of the shirt to spark the curiosity of others” — or gauge their interest.

Alternately, he said, you could opt for a blazer or even a suit, though that approach takes you closer to an aesthetic popular in the early-to-mid 2000s known as “indie sleaze.” (That period is in the midst of a major trend cycle, so it actually feels contemporary.)

Another potentially more versatile option is to wear the T-shirt under a button-up shirt of your choosing, leaving the top two buttons undone. Just make sure, Mr. Bernstein said, that you pair the tee with a good watch or other form of jewelry and good shoes. Then you have what Mr. Caramanica called “the correct blend of upright and lowdown.”

Kind of like: There’s more going on under here than you might imagine. Hint, hint.

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.

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