Jonah Weiner and Erin Wylie’s blend of insight and humor has drawn tens of thousands of subscribers to Blackbird Skyplane

Subscribers to the Blackbird Spyplane newsletter never quite know what’s going to arrive in their inbox. A post might be dedicated to business shirts found on eBay, an essay on the trend cycle in the internet age, an “auntwave mecca” in Niki de Saint Phalle’s Tarot Garden or style interviews with the likes of Jerry Seinfeld, Rashida Jones, André 3000 and Nathan Fielder.

With its playful snapshots and crudely spliced Photoshop aesthetic – reminiscent of dial-up internet – the “sletter” describes itself as “your No 1 source for style, culture, & ‘unbeatable recon’”. The combination of ahead-of-the-game insidery insight, a goofball sense of humour and private language – a mix of streetwear slang such as “jawn” and “swaggy” and fighter jet lingo – has seen BBSP ranked highly in Substack’s culture newsletters. Its subscriber numbers are in the tens of thousands and include the likes of John Mayer, Lorde and Ezra Koenig. The Instagram account, meanwhile, is followed by Lena Dunham, Mark Ruffalo, Rashida Jones and Ella Emhoff.

BBSP was founded by the culture journalist Jonah Weiner and his partner, Erin Wylie, an Apple design talent scout, in April 2020. Weiner, the more vocal of the duo, describes BBSP’s tone of voice as “a filtering effect”. Speaking on a video call, he says “X out of 10 people are going to hit this wall … and their eyes will cross and they’ll say, ‘this is not for me’, but for the Y out of 10 that stick around, they’re going to feel in on something.”

The duo are long-term style obsessives, which gives them an uncanny ability to predict what might be in mainstream wardrobes six months from now. While he downplays a “crystal ball” factor, Weiner does concede it happens. “Last November we did a thing about silver sneakers, the running Y2K era kind of aesthetic,” he says. “There was something that felt almost gross to put in the newsletter … Now one of the hottest sneakers out is the Asics Gel Kayano, which is exactly that kind of shoe.”

BBSP is an arbiter of what is in and out, but it has little of the snark found in fashion publications or sneakerhead forums (its chatroom, Classified Spytalk, is endearingly earnest). In the Spyplane universe, an “if you don’t have anything nice to say …” wholesomeness prevails: “I almost have to bite my tongue when I’m in newsletter mode, because we just lead with what we like and if we don’t like it, it doesn’t come up.” The exception here is Amazon, regularly the subject of derision. Weiner describes the site as “an enemy in the Blackbird Spyplane cosmology”.

The laidback “posi” POV may be influenced by location. The couple is from the east coast – Weiner was born in Brooklyn and grew up in Staten Island, while Wylie is from outside Philadelphia (“Side note, ‘jawn’ originally is Philadelphia slang,” says Weiner proudly). They moved to Oakland eight years ago.

Weiner says being in Oakland “allows you to encounter different ideas” in terms of style “like crunchy, old people in the organic produce section of the grocery store, wearing very Bay Area specific outfits”. There’s also a bicoastal synergy that plays to BBSP’s advantage: “For any number of reasons, the cool kids in downtown New York, a lot of them want to dress like old crunchy people in the produce section of the Berkeley supermarket. So it’s a happy coincidence.”

This outdoorsy Californian look – fleeces, hiking sandals, boonie hats – is often described as gorpcore or, to use the BBSP term, gorp. It’s one that the newsletter has continually championed. But, with the look now on the radar of mainstream outlets like Vogue, is it over? “The original gorp moment actually happens in the early 90s, when you’ve got kids in the New York outer boroughs, and then early Wu Tang videos and early Mobb Deep videos, catching wind of these brands like North Face … and wearing those clothes in an explicitly non-outdoor adventure context ... I feel [it’s] part of my own biography, and so I’m eternally interested in wearing clothes like that.”

Ultimately, it’s this idea of personal style above all that BBSP tries to promote. “Fashion is a language and you can’t get outside of language but I think that you can be more or less beholden to this manic whiplash mode of trend chasing,” says Weiner. “We’re interested in trends but it’s more than ‘This is the thing you need to care about this month.’ It’s more how do you weave [in] your own biography and things that you consider recurringly true about yourself and your interest.”

The newsletter’s profile is growing.

BBSP released a small run of merch – caps and T-shirts – in 2022, and a spin-off newsletter, Concorde, helmed by Wylie, launched this month. Weiner says there is no “gender coding” at BBSP. Concorde is more focused on female readers but “speaking as a dude who’s interested in clothes, I’m interested in reading Erin because even if she’s linking to, say, dresses or other garments that I don’t personally wear … how she covers it is going to help me understand clothes better and dress better.”

Weiner is resistant to expanding much beyond the inbox. He says the pair make a small amount of money from affiliate links to eBay and bookshop.org, but any branded content – the bread and butter of many newsletters – would be considered extremely carefully. BBSP subscribers pay $5 a month or $50 a year which, even if only half of all subscribers pay, adds up to a decent sum. This has had an impact on the BBSP life, with Weiner now working on the newsletter the majority of the time. Was that always the plan? “I did this interview with the painter, Issy Wood, and she does music on the side. She had a dalliance with a label and her top line takeaway was: don’t professionalise your hobby, because anytime you do that you’re reconfiguring your relationship to something that gave you a quote unquote pure thrill. On balance so far, the newsletter just still feels like a fun hobby, even if it’s one constantly on my mind.”

BBSP’s essential style guide for autumn

1 Wearing two button-up shirts at once. You’ve spent spring and summer wearing one shirt like an ascetic. Now the weather is cooler, meaning you can get gluttonous with shirts. Is one shirt hanging open over the other? Are both buttoned? Are they both patterned? It’s up to you.

2 Wearing a hat over a hoodie. Another deceptively simple move that conveys just the right amount of what some people would call “ridiculousness” but we correctly identify as “joie de vivre”. It’s an appealingly unconventional way to layer, and it creates a pleasing shape, especially but not exclusively with a bucket hat – knit beanies can be very cool over hoodies, too.

3 Mizuno and Brooks running sneakers from the early 2000s into the early 2010s. A trove of overlooked epiphanies whose time has come.

4 Buying nothing on Amazon or Doordash or Good Eggs, etc. Convenience is overrated. Get out of the house and be around other people – a small step with many beautifully and profoundly pro-social ramifications at a moment when companies want us to be alone all the time for some reason.

5 Look at things through binoculars. Trees, songbirds, lichen growing in high-up places, farm animals if you live near a farm … These are all nice things to look at through binoculars, which means, among other things, time that you will not be looking at a screen, and a great way to experience the simple but powerful truth that sustained attention can be trippy.

ncG1vNJzZmivp6x7tbTEoKyaqpSerq96wqikaJ6RqLWqu81oaWlqYmS7sMKOaXBompyWsKyuyKubZqugrr2trc2eZKedp6i5psDTnqlmop%2Bjrql51p6gp52iYravwMSrraKdpw%3D%3D