Blackbird Spyplane are the coolest people in your inbox

Photographs Nicholas Albrecht

When it comes to work, I am not normally a particularly nervous fellow. Over the years, I’ve reported from Mafia-controlled towns in deepest southern Italy and gang-conflict-mired estates in southeast London. I have spent no shortage of time with con-artists and swindlers, thieves and violent criminals. Why, then, did I feel so jittery before meeting Jonah Weiner and Erin Wylie, the couple behind Blackbird Spyplane, the cult fashion and culture newsletter? For one thing, no one likes feeling self-conscious about what they’re wearing, though I needn’t have worried too much. I eventually settled on a plain white T-shirt and multicoloured zip-up, and sweet validation was not too long in coming. “We see the jacket king,” said Weiner, a baseball cap-clad, neatly bearded figure in his mid-40s, when we first met. Wylie – blonde, light knitwear, air of engaging earnestness – smiled with what I hoped was encouragement.

Blackbird Spyplane’s mission statement is straightforward. For the past five years or so, it has been “Your No 1 source for ‘unbeatable recon’ into style, travel and culture.” Twice a week, every week, new content is primed by Weiner and Wylie, before being launched into the inboxes of its tens of thousands of subscribers. The subject matter is not prescriptive: a mishmash of fashion, books, music and recommendations, travel guides and think pieces, whatever takes the couple’s fancy on a particular week. The tone is witty and irreverent; welcoming, rather than sneeringly elitist, though Weiner has no qualms in making sweeping pronouncements on matters ranging from the vulgarity of grey T-shirts to the intrinsic worth of the humble hoodie. Its dominant aesthetic is of the deliberately shabby early internet, a riot of gaudy colours and bad photoshopping. “We’ve gotten a bit better over the past five years,” Wylie laughed. Though not too good, Weiner shot back. “It’s something that communicates there’s actual humans working on this thing.”

Broadly speaking, Blackbird Spyplane – the name derives from a Cold War-era American reconnaissance plane – is a celebration of the things the couple love rather than a denunciation of the mediocre or dull or grotesquely self-important. “We still believe,” Weiner wrote last year, “that cool clothes (and other cool things people make) can be sick talismans of human ingenuity and vessels of interpersonal connection.” Such enthusiasm is evident from your first encounter with the newsletter, or sletter, as they refer to it in writing. “We can be critical about things,” Wylie told me, “but if we’re just going to shit on something, we don’t need to write about it.” There are exceptions; Amazon occasionally takes a kicking. “Criticality is really important,” Weiner said. Still, arriving in someone’s inbox multiple times a week meant its own specific brand of intimacy. “You don’t want people to think, ‘Oh here’s this fucking asshole marching in here, talking shit about everything.”

Just £5 a month grants you access to a range of exclusive content: essays and thinkpieces on topics ranging from male hair-loss to lengthy examinations of something called “the ugly genius matrix” and the very notion of personal taste. The members’ chatroom is a lively, relentlessly earnest place, full of contributors trading style and travel tips. In 2022, the couple launched Concorde, a twice-monthly offering run by Wylie, aimed slightly more precisely at a female readership, though the couple have stressed that “insights, intel and ‘cute swag information’ transcend gender”. Weiner and Wylie were inducted into the Business of Fashion 500 – a global index of fashion’s prime movers and shakers – in 2024. Things are going well enough that Wylie was able to quit her job at Apple a couple of years back, while BBSP consistently hovers in Substack’s top 10 culture newsletters. If they are leery of sharing precise figures, quick cigarette-packet calculations put the newsletter’s annual turnover easily in the six figures.

I met with Weiner and Wylie at a reassuringly trendy pizza restaurant in Oakland at the end of last month. They are native East Coasters: Weiner grew up in New York, Wylie in the suburbs of Philadelphia. But they have been based in the Bay Area since the mid-2010s. (The laid-back, unselfconscious style of OAPs in their local supermarket has been a key influence on their conception of style, they joked.) The newsletter began in the dog days of the pandemic, when they glimpsed an opportunity buried in the stasis of the enforced shutdown. Weiner, a contributing writer at the New York Times Magazine, best known for witty celebrity profiles, and Wylie – then a design scout at Apple, with her own long background in magazine editorial – found themselves with lots of spare time and no shortage of ideas to fill it with.

The way they tell it, BBSP’s origin story is simple enough. “I was at home from work,” Wylie said. “We were doing a lot of neighbourhood walks and we wanted to do these eBay dives, we wanted to do interviews… We wanted to talk to people.” For Weiner, the pandemic put the brakes on the sort of reporting he’d been doing for the best part of 20 years. “You know, travelling to spend time in the orbit of people who were good at making things… It was a way of getting people on the phone. And though I’d written about people who cared about clothes, I’d never actually written about clothes. It was purely a hobby.” Unsurprisingly, both Weiner and Wylie are long-time thrift-store and eBay super-sleuths. “We’ve been doing both for a long time,” Weiner said.

Wylie picked up his point: they have always had an affinity with people who made things, she said, whatever the discipline. They just liked to understand the mechanics of the things they liked, as well as being around the people who brought them into the world. It didn’t feel intimidating or strange, starting a blog at their kitchen table. “It’s something I’ve been doing since the 90s as a teenager. It felt like a low-stakes thing to do. And it was just really fun,” Wylie said. For Weiner, there was another, even more obvious factor at play. “I like writing. And I wasn’t doing any because I wasn’t doing any reporting.”

We are living in a golden era for style content, in quantity if not always quality. The creative possibilities offered up by the online age have witnessed a blooming of a huge number of Substacks and podcasts, the likes of Throwing Fits and How Long Gone chief among them. They offer consistent, sometimes maddening, opinions and worldviews, presented with a mixture of high sincerity and gently coaxing irony. Herein lies the central appeal of Blackbird Spyplane. To the extent that old-school fashion journalism exists beyond barely concealed advertorials and PR-manicured profiles, it often alternates between overt bitchiness and borderline illiteracy. An email newsletter will never be as intimate as a podcast, where listeners can fully submit to the voice floating in their headphones. But it can come reasonably close. “It’s a cousin of intimacy,” Weiner said. The couple have a few steadfast rules, aimed at preserving their integrity and independence. No affiliate links, for one. If readers are parting with their money, then they should be able to expect unbiased recommendations, is their reasoning.

Over the course of his career as a magazine writer, Weiner has worked within the constraints of the form. He has profiled Seth Rogan, David Fincher, Nathan Fielder and Bong Joon Ho, and his style will be broadly recognisable to anyone with a passing familiarity with American magazine journalism: lucid, witty, entirely comprehensible. The earliest Blackbird Spyplane was not exactly that. Instead, Weiner set about developing a style that might best be described as millennial-dadaism. Some of the earliest questions posed by the newsletter included: Would socialism KILL cool clothes?? Is swag genetic?? What’s AFTER FLEECE? And: Are you wearing CURSED GORP?? The accompanying prose felt both highly caffeinated and cheerfully freeform. Having spent a considerable amount of time with it, it began to feel like the sort of hypnotic, highly idiosyncratic manifesto that Ted Kaczynski, the Unabomber, might have written if he’d traded domestic terrorism for trend forecasting.

To suggest that Blackbird Spyplane is, or has ever been, something like performance art would be doing it a disservice. The week before my trip to California, the newsletter published an intriguing piece on a bizarre series of Instagram posts from the menswear brand J.Crew, featuring AI-generated models and photoshoots. “J.Crew used AI to counterfeit their own vibes,” ran the BBSP headline. The scoop was picked up by the New York Times and The Cut, among other outlets, was well as Good Morning America, one of the country’s largest morning news shows. “They actually got the name right. They didn’t call it Blackboard Sky Plane or something… It’s sort of a funny moment where you can be this sort of definitionally niche newsletter, but still find your way on to Good Morning America,” Weiner said. “They didn’t reach out to us for comment,” Wylie said. “They just cited the website”. J.Crew’s response was swift enough: a small amendment to their initial post to include mention of the “AI photographer” behind the self-styled “digital art”. As Weiner noted in a follow-up piece, the debate occasioned by their scoop had been lively. “The general tone”, he wrote, “is that cool people regard this shit as depressing and wack.”

The regard of cool people is an important part of the newsletter’s mystique. It is, as the weight of press coverage makes abundantly clear, almost obligatory to itemise the celebrities who subscribe or follow the BBSP Instagram page. Lorde, Ezra Koenig and John Mayer chip in their £5 a month on Substack; Mark Ruffalo, Lena Dunham and Rashida Jones are among other distinguished followers. The newsletter also carries a regular interview series with the great and good, distinguished by an ungrovelling tone and witty, leftfield questions. It’s a winningly diverse archive. Adam Sandler – “a tight 15 minutes on the phone”, grinned Weiner; Jerry Seinfeld, Andre 3000, Nathan Fielder and Kim Gordon number among the “delightful and definitive conversations about life, happiness, creativity, swag, and cherished rare possessions”.

I wondered if being based in the Bay Area had helped the couple preserve their editorial independence. It must be tougher to preserve criticality – or indeed their much vaunted positivity – if they were perpetually mired in the cynical New York media world. “I’m from the city and very much hold a New Yorker identity,” Weiner replied, “but when I go back I often find myself in a room full of writers, ego-jousting.” If it was disconcertingly easy, he said, to slip into disaffected New York media-mode, it didn’t take too much to climb back out of it. “I was like ‘this newsletter, it’s corny, it’s weird, it’s earnest… how am I sending this thing out?’ That’s just one example of why it’s good having distance from the epicenter.” Caring from afar meant less risk of being consumed by its accompanying bullshit. Plus, they’re in a different stage of life now. “We’re not going to fashion shows,” Wylie said. “We’re going on hikes.” The paradox lay in the fact that they still cared deeply about the industry and its inner workings.

In the days leading up to our meeting, I’d embarked on the usual round of dutiful research. There was the Spyplane archive to sift through and podcast appearances – Weiner’s turn on Throwing Fits was entertaining, if slightly remorseless in its chumminess – to scour for stray detail. I consulted previous magazine interviews to try and avoid the same, likely stale, exposition-heavy questions. No relevant blog went unread in my quest. And yet, I still could not find a particular answer I searched for.

As we waited for our main courses, I explained that I was thinking about my partner of almost eight years. A woman of impeccable taste, there is no one else in the world I trust more on matters of fashion or general discernment. We are lucky enough not to regularly bicker and there is plenty of healthy mutual respect in our day-to-day life, on matters great and small. All of this being said, if we had dual responsibility for running and growing a weekly newsletter, I suspect it would take, say, two months before she’d attempt to bludgeon me to death with a frying pan. How on earth had they made it work for over half-a-decade and counting?

“You don’t know until you try it,” Wylie offered diplomatically. “Give it a shot,” grinned Weiner.

Before our meeting, I had approached the newsletter’s voluminous archives with both admiration and something like creeping horror. The idea of summoning new, even jokingly authoritative things to say about fashion and culture every single week felt like a very quick route to madness. Did they ever, I ventured, feel pressurised by people treating them like trend-forecasting oracles?

“No one’s ever said that!” hooted Wylie.

“Thankfully I’ve never heard anyone call us that,” Weiner added. “I thought you were going to say something horrible like ‘giant assholes’. I think if anything there’s a lot of ironically calling ourselves, I don’t know if we’d use the word ‘oracles’, but like ‘clairvoyant’ or ‘omniscient’… We’re sort of taking the piss.”

This gentle irony has bamboozled some readers and alienated others. On one Reddit post, a commenter was incredulous that Weiner had proselytized against grey T-shirts, to the point of declaring them forbidden. Another decried its increasingly namedroppy “LA-vibe”. Others, however, defended its good taste and strong, consistent values.

It is not to everyone’s taste. There are those that consider the heavily stylised, self-generated slang and pervasive zaniness offputting, even if some of the more exhausting commitment to “the bit” has been dialled back in recent years, with Weiner’s prose becoming markedly less free associative. This is, to my mind at least, a pleasing development. As much as I have enjoyed the newsletter and often partaken greedily of its bounties, it is difficult for an Englishman in his early 30s to even ironically get on board with referring to drip, swag, or the “slappiest clothes”.

In fairness, neither Wylie or Weiner have ever aspired to pleasing everyone. If you like it, you like it. If you don’t, no hard feelings, the unsubscribe button is a click away. “Jonah has always had a persona in a way. I think it was this really fun performative outlet for him,” said Wylie. “He was doing all the writing in the beginning. I’m really glad that we talked about things early on and decided to lead with excitement and positivity. Because we’ve gotten that back.”

I admit that a niggling voice in my head had half wondered whether the house style might be hiding a darker truth. That behind the good vibes, lay two calculating fashion industry types. During our hours together, the couple were unflaggingly jovial company, listening intently to each other’s points and treating my slightly freeform questions with consideration. Phoning-it-in is not an accusation that can be levelled against either of the couple. For its devotees, the newsletter’s appeal lies in being part of an inclusive community. In the middle of the fray, rather than outside staring balefully in. “Like we’ve created a really positive space on the internet,” Wylie added. How many people can really say that? A place where earnestness was a function not a bug, while managing to retain its cool. An almost impossible task, in other words, which Blackbird Spyplane continues to make look easy.

The Peanut Vendor: This is one of the most incredible places to find secondhand furniture and design in the world, located right by Victoria Park in Hackney. Co-founded by Barny Read and Becky Nolan in 2008, their focus is on early to mid-20th-century pieces from Italy and France. They avoid all kinds of prevailing trends and clichés. We followed them on Instagram for years, finally popped in, and were immediately fantasizing about filling a shipping crate.

The Relaxed Farmer Shirt: Conkers is a tiny, emerging clothing line out of East London; they make clothes from materials and fabrics grown and loomed in the UK. Designs tend to be inspired by the British countryside, but in clever, surprising, non-fusty ways. The Farmer Shirt is one of their simplest, most charming styles.

A day trip to the Charleston Farmhouse in Firle: This is the Bloomsbury Group’s Sussex hangout, almost every square inch of which has been painted or personalised in some idiosyncratic, charming, beautiful way. Preserved as a museum now, has to be seen to be believed.