Invents a new language to talk about style

Blackbird Spyplane is a newsletter written for enthusiasts: rabbit hole shoppers who store extremely specific saved searches on eBay like it’s a competitive sport. There’s nothing casual or low-key about it, other than a core appreciation of that kind of thing crunchy outdoor clothing once associated with chill and quiet people.

This is largely due to the intense voice of the newsletter, which reads like a parody of a neurotic online men’s style writer – things he likes are “dope”, “brand”, “tasteful”, “vibey” and ” crazy cool.” sometimes in headlines — but is closer to a hyperbolic version of the inner monologue of Jonah Weiner, a journalist who started Blackbird Spyplane in May 2020 with Erin Wylie, an industrial design talent scout for Apple. (Mr. Weiner is a contributing writer for The New York Times Magazine.)

Beneath the overstimulated voice, however, there is sincerity. A newsletter that began as an outlet for “invincible recon” — fashion, culture and interior design recommendations — and interviews with creative types about personal style has increasingly become a space for Mr. Weiner, who typically writes the newsletter, and Ms. Wylie, who edits it, to indulge their obsessions.

Sir. Weiner and Ms. Wylie, who lives in North Oakland, Calif., has positioned himself free of advertiser influence, as do zine writers. Like zine writers, their audience is quite small by digital media standards, but not insignificant. Blackbird Spyplane is hosted on Substack, which does not release specific subscriber numbers, other than to say the newsletter has “tens of thousands” of subscribers to the free version, while “thousands” pay at least $5 monthly for additional content.

In the first year, the pair hunted for novelty items and vintage ceramics and asked famous people about their niche shopping interests. They still do, but they also publish longer essays on male pattern hair loss and cars’ curious color trends; advice on how few friends and “officer” responsibly (or not at all); decrees against things they believea skirt,” like heather gray t-shirts; and theses about why the aesthetics of 1990s coffee shops (shabby) are superior to modern coffee shops (Scandinavian). Everything is still illustrated with deliberately chaotic Netstalgic graphics.

“When it comes to style and fashion coverage, so much of it these days feels like marketing,” Mr. Weiner said. “There are a lot of people who like the Internet best when it feels handmade and misshapen and idiosyncratic.”

Substack doesn’t provide demographic information even for its newsletter creators, but anecdotally Blackbird Spyplane has a large media following, which makes it seem influential. Kaitlin Phillips, a publicistsaid via email that “getting my client in Blackbird is the best way to send a mass email to all fashion writers in New York, menswear and womenswear.”

But while the newsletter has attracted female readers and Q. and A. topics – like Sandy Liang, who spoke to Blackbird Spyplane about buying Polly Pocket toys on eBay, coveting a pair of Skechers she was denied as a child and other “things that shaped me as a designer, but I feel like it’s not flashy enough to other people can care,” she said — its content has long been seen as “dude-leaning,” which Ms. Wylie said, or “male-coded,” which Vox once put it. Absorbing the voice can at times feel like watching Dr. Jekyll (if he were a socialist) overcome Mr. Hyde (if he was a hypebeast), with one dressed in vintage LL Bean and the other in Homme Plissé Issey Miyake.

Ellen Van Dusen from the household and clothing line Dozen Dozen joked that the style had a “learning curve.”

“The first time I read it, I was like, ‘This is crazy. I don’t even know if I can decipher what they’re trying to say here,'” she said. The second time I read it, I was like, ‘OK, this is performance art. It is fun. It’s a joke.’ And the third time I read it, I was like, ‘Oh my God, there’s so much valuable information in here.'” (Ms. Van Dusen once cooperated on a line of jackets with Ms. Wylie.)

And last week, Blackbird Spyplane got a little less dude-inclined, with the introduction of a new vertical of Ms. Wylie, focused more on women’s fashion. It’s called Concorde, in keeping with the supersonic jet theme, and is written in her voice: relaxed, loose because anything else “would feel really put on,” Ms. Wylie said a few days before the first issue was sent to all subscribers. (In the future, Concorde will be published twice a month for paid subscribers.)

“It’s her version of a much less insanely crazy prose style than I do,” said Mr. Weiner, who switched roles with Ms. Wylie as her editor for Concorde. “If anything, I thought, ‘You don’t need to make superlatives with all the heads here.'”

That’s because the Blackbird Spyplane voice, no matter how different it is, isn’t everything to them. They think their readers respond more to the energy behind it, “the notion of: This thing is going to show up in my inbox and it’s just going to be fun,” Mr. Weiner said. “This is not a corporatized, algorithmic, AI version of a funny, friendly voice.”

“You could design an AI to serve the various things we connect,” added Ms. Wylie, who used her first Concorde deployment dissecting her interest in the color silver and connecting a plate of Roman anchovies to a Bjork video for the 1990s designs by Martin Margiela. “But I don’t think anyone would.”

Ms. Wylie emphasized that the “spinoff” would still have a unisex flavor, “because anyone can wear anything,” she said, and because that’s how she defines her personal style. She and Mr. Weiner, both 41, are a longtime couple (though they would not say how many years they had been together), and they deal in clothes. He recently took ownership of a pair of her Lauren Manoogian pants.

But from the earliest days of Blackbird Spyplane, Ms. Wylie has wanted to dig more into women’s fashion. She spent about a decade editing and writing for magazines, and before that she worked at a fashion forecasting firm. Two things have held her back: demands on time from her day job and the fact that she and Mr. Weiner is “erring on the side of being anti-growth,” as he put it.

“We just have a general foot-on-the-brake approach to this thing in terms of expanding it,” Mr. Weiner said. “We have no problem staying niche.”

It extends to the way they make money. They have turned down offers from big luxury brands, like a French fashion house that wanted them to embed its latest collection video in the newsletter, and an online retailer that wanted to collaborate on a capsule dedicated to small producers.

“Erosion of genuine editorial” is why Ms. Wylie said she left magazines in the first place.

“Everything I was asked to do was sponsored or advertised and it just didn’t feel right,” she said.

They also don’t accept gifts, an exceedingly rare policy in an ecosystem where brands shower fashion writers, editors and influencers with expensive bags and all-expenses-paid trips in exchange for content. They claim to earn newsletter related income only from subscriber fees, rarely merch drops once they made shoes with a Finnish shoe brand called Tarvas – and minor earnings from purchases made through affiliate links to eBay or Bookshop.

“There’s something obviously dusty and throwback to this mentality, but we’re fine with being dusty and throwback this way,” Mr. Weiner said. (If that sounds like a scrappy operation, consider that Blackbird Spyplane has brought in big names as interviewees, including Seth Rogen, Lorde, Jerry Seinfeld and Andrew 3000some of who Sir. Weiner has separate profiled. Its earnings most likely add up to six figures annually.)

“You open any fashion magazine right now and I guarantee you there are a lot of clothes in there that none of the staff at the magazine think are particularly cool,” said Mr. Weiner said. “They’ve made advertisers happy. If there’s anything in this newsletter, it’s because we think you’ll like it. It’s a very straightforward proposition.”

As straightforward as possible for a newsletter that in its latest issue used the following phrases: “cerebellum-bussin quasi-paradox,” “striking ‘plant-based’ seizures,” “jawn-polytheistic spin,” and “roasted & toasted footwear.”

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