The city is woollier than it’s been in a while — everyone seems to be crimping the usual boundaries. E-bikes and scooters zip through the middle of the street, and restaurants have annexed the pavement outside their doors in hopes of keeping their businesses afloat. After a brutal spring and summer of pandemic uncertainty and economic instability, New York is doing its best to pass for its old self, but in truth, things haven’t felt this unsteady since right after 9/11.

In this context, shopping for anything other than essentials has felt foolish verging on irresponsible. I’m still haunted by the last item of discretionary clothing I bought before quarantine — so much so that I won’t share it here. Even now that stores are open, that humble jolt of electricity you feel when touching a new, covetable garment is almost always dampened by the rank sweat gathering beneath your mask.

I write this as very much an anxious skeptic who still rushes through the supermarket. Even as stores have reopened, I’ve mostly avoided them, no matter that the scientifically driven portion of my brain understands that, in short bursts, it’s relatively safe.

These are precisely the challenges that outdoor shopping is equipped to address, though, and over the last couple of weeks, I’ve passed through several of the city’s reopened flea markets and other streetside sales. Even with limited choices, shopping en plein air was a kind of relief, an opportunity for a change of scenery, a tentative step toward community (and, you know, new stuff).

In June, as turmoil across the country was hitting a fevered peak, I noticed videos on Instagram advertising a street sale in McGolrick Park, in Greenpoint. The BLM Sidewalk Sale, organized by Aaron Wiggs, Perry Goodman and Sachiko Clyde, was a loose affair, and its aims were charitable. I still wasn’t ready to break quar, but when I finally made it to one of the sales, which took place throughout the summer and just came to a close — each installment was advertised with hilarious D.I.Y. videos on Instagram — it was heartening to see vendors and attendees masked up and maintaining as much distance as retail allows.

Largely made up of clothing sellers (new and vintage) — including, at various times, Chloë Sevigny, Haley Wollens, Miyako Bellizzi and Bella Hadid — the sale was less about the specifics of the items on offer than the relief that came with gathering with people and the sense of civic duty that came with knowing all proceeds — I bought a ball cap from the Cookies Hoops podcast ($25) — would be donated directly to those in need.

All told, the sales raised more than $265,000 for various charities (Justice for Elijah McClain, Building Black Bedstuy, Equal Justice Initiative and many more) and struggling local businesses (Punjabi Deli, Julius’), a stunning display of decency via ingenuity and moxie. If there were a way to make the BLM Sidewalk Sale a regular, continuing affair, it could easily become a New York institution.

Which is to say, it could live side by side along some longer-running markets, which have recently restarted following long gaps. The Chelsea Flea (West 25th Street between Fifth and Sixth Avenues) is back up and running, with its familiar blend of furniture, artwork and vintage clothing. I was most intrigued by a vendor selling old architecture books and copies of After Dark, a theater, downtown culture and gay interest magazine from the 1970s.

In Dumbo, the Brooklyn Flea (under the Manhattan Bridge arch) recently reopened, and it is perhaps the most ambitious of all the outdoor markets. The amount of vintage clothing is impressive, though mostly for women. After an hour spent poking through racks, I found the ultimate consolation trinket for a foiled shopper: “The Shopping Bag: Portable Art” ($10), a book celebrating the graphic design of store bags.

I fared better at the Hester Street Fair (Seward Park, corner of Hester and Essex Streets) on the Lower East Side, which in general skews younger and more vibrantly eclectic than the other markets. I went during a vintage-focused weekend last month and — after having my temperature checked at the entrance, the only sale to do so — found a green Gouge lowrider-themed graffiti art T-shirt ($20) sold by Lawrence Woods, who runs the @vanitythread Instagram account.

More surprisingly, I saw an old friend, William, who had taken a booth along with some pals who were offloading things from their closets. I persuaded his friend Scott to sell me a pristine pair of vintage Nike ACG patterned shorts for $20. (All of this made me miss the old Kinfolk Dude Sales in Williamsburg — someone please bring that back when it feels right. R.I.P. Kinfolk.)

Thanks in part to the agreeable weather, and in part to what I imagine was a long, quarantined summer of confronting personal shopping excesses, there now appears to be a surge in stoop sales, advertised on Instagram and TikTok or via signs posted up on Williamsburg light poles.

Last weekend, I saw a posting for one by Janette Beckman, the photographer behind so many iconic 1980s hip-hop portraits. When I arrived on Bond Street, there was a splay of tables from her and her friends and a crowd of people happy to be chatting. I watched as a friend negotiated T-shirt prices with Charlie Ahearn, the director of “Wild Style,” and I bought one of Ms. Beckman’s recent chapbooks ($10) as well as an oversize zine of socially apocalyptic photos shot at Woodstock ’99 by Mike Schreiber ($20), who signed it before handing it over.

Afterward, I headed downtown to squeeze in a visit with Chad Senzel (@chadsenzelarchive). A week before, I’d caught up with him when he was selling from a rack in Dumbo and bought a plaid winter-themed Tommy Hilfiger button-up ($25). Like many in the post-Procell ecosystem, Mr. Senzel and Mr. Woods specialize in the sartorial ephemera of the 1990s and 2000s: rare band T-shirts, bootlegs and not-yet-fully-commodified designer vintage.

This time, he was teaming up with another dealer, Cole Star (@csillag_usa), with an impromptu setup of racks on Orchard Street just down the block from the seemingly permanent scrum outside Scarr’s Pizza and just around the corner from Dimes skate park. I spied a sharp piece Mr. Star was selling: a 1990s Polo Ralph Lauren camp-collar shirt with a print depicting elegantly dressed gentlemen of, I’m guessing, the 1950s ($45).

I tried it on, had Mr. Senzel shoot some pictures on my phone, and looked at my reflection in the window of a parked car. It had all the hallmarks of great shopping — a bit of happenstance, well-tuned customer service, the sense that you’re getting something you might not see anywhere else. For now, it’ll do.