How Choire Sicha Is Steering Style in a Crisis

The man behind the curtain of the New York Times’s most innovative section emerged fully formed from the Internet. But the Style section's reputation for lightness is running up against our chaotic moment.

by | July 27, 2020

Art by Shawné Michaelain Holloway


Editors of the New York Times’s Style section gather for a meeting every Tuesday. In late May, “someone asked a great question,” Choire Sicha, the section’s editor since 2017, told me “They’re, like, ‘How much rich people should we cover versus everyday people? Why do we do these things? What are we?’” Sicha explained. “And we just sort of got to talk about, like, why do we assign stories even?”

The year 2020 has seen police murder numerous Black Americans, the abuse of peaceful protesters, millions of people fall out of work, and the national death toll from COVID-19 skyrocket to over 140,000. The responsibility of a free press is magnified. And, of course, the consequences of getting it wrong are magnified as well. The pressing topics of our moment aren’t what we usually think of as Style stories, which creates a certain quandary. How does a section known for lightness stay relevant in one of the darkest chapters of recent history?

The Style section of the New York Times debuted in 1992, then called “Styles of the Times.” A press release at the time heralded an article about “haircut malpractice insurance for nervous salon owners,” along with street style photographs by the late Bill Cunningham. Early topics covered in the section included shopping, fashion, dining, relationships, and weddings, and most of those topics are still covered in Style today. Over the decades it has accrued a reputation for eye roll-inducing trend pieces and trollish real-estate coverage — tales of the wealthy that we love to hate-read. (Anyone remember that time monocles were (supposedly) a hot new fashion trend? No one?)

In recent months, however, the Style section has covered quarantining with ghosts, “mask acne”, pandemic beards, and what city rats are up to (answer: nothing good). The section has also published a wide-ranging Juneteenth package, an explainer about the term BIPOC, and stories about street medics and bail reform funds. As news keeps breaking and daily life unexpectedly changes for every one of us, Style will have to continually negotiate what matters to its readers. “A lot has changed in — I don’t want to say good ways,” Sicha said in an interview conducted on May 26 from his home in the New York City suburbs. “We’ve had to be intentional about what we’re doing.”

This puzzled me a bit. We’re talking about the New York Times, after all. Hasn’t the Style section always been “intentional” in its coverage, I asked. “I don’t know,” Sicha said. “I don’t know. I don’t know if I have a good answer.” But if anyone is prepared to discover how to cover glossy fare alongside desperately serious issues and describe our lifestyles even when social life as we know it doesn’t exist, it’s the enigmatic, slightly mercurial Choire Sicha.

A native of internet culture, Sicha has been an influence on digital media since the beginning of the blogger era. The signature voice he developed over the past two decades — a blend of irony, self-dismissal and self-consciousness — seems uniquely suited to the uncertainty of this moment, as well as reimagining what Style means at the  New York Times.

Sicha is charming and warm, and he’s more transparent about the journalism industry than the vast majority of people at his level of authority. Yet there’s an inscrutability about him acknowledged even by his close friends. He “doesn’t give away a lot of stuff about himself,” said the novelist Emily Gould, who has known Sicha since they worked together at Gawker in 2006. Gould compared him to a mirror, reflecting back what a person wants to see in themselves. “The most important thing, probably, is that he is a Scorpio,” Gould explained. “He’s mysterious and charismatic and will never give you a straight answer.”

During our half-hour conversation over Google Meet, Sicha used the phrase “I don’t know” 18 times. That uncertainty from a New York Times editor was disarming, if somewhat frustrating for my interview. He also didn’t sit still: At one point during the video call, Sicha walked offscreen and returned with a long scarf. While talking, he wrapped the scarf around his torso, tying and untying in front. In the moment, I couldn’t tell whether he was nervous about the interview, bored by my questions, or fidgety after a long day in front of his computer. The self-consciousness he inspires, it turns out, is not uncommon.

“There’s something about his personality that’s sort of, like, malicious, but it’s in this very playful way,” Gould said. “He’s sort of this trickster God figure. He likes to fuck with people, but in a way that leads to something interesting or creative.”

Raised in Evanston, Illinois, Sicha didn’t attend college. He worked in HIV/AIDS education on the West Coast during his early twenties. When Sicha arrived in New York City in the late 1990s, he worked at a Chelsea art gallery, Debs & Co (and later memorialized his gallery-hopping habit in a 2003 piece for The Morning News). Ben Widdicombe, a former gossip columnist, believes he met Sicha at a party in Gawker Media founder Nick Denton’s apartment in the early 2000s. At the time, Sicha had leveraged what he refers to on his personal website as “amateur blogging” into a gig at Gawker. “He was this art-world gay who got this nutty side gig putting words on the Internet, but we weren’t necessarily sure it was going to go anywhere,” Widdicombe recalled.

The nutty side gig did go somewhere: In 2003, Sicha replaced Elizabeth Spiers,’s founding editor. A year later, he was promoted to editorial director of Gawker Media. Sicha’s personal writing and his tenure as editor helped establish what has been referred to as “blog voice,” which did much to set the general tone of the Internet before the dominance of social media in the early 2010s. Sicha’s approach was hugely influential for a generation of young writers: smart but not academic, funny but still thoughtful, personal but not narcissistic, and above all, skeptical of power brokers.

Like Spiers, who left Gawker for New York magazine, Sicha then heeded the siren call to legacy media. In 2004, six months after his promotion, he went to the New York Observer, an uptown newspaper (now formerly owned by Jared Kushner), for a senior editor gig. But Sicha returned to Gawker in February 2007, this time as managing editor. His second tour of duty was rough, even by the draconian standards of digital media. In April 2007, Gould, then his employee, appeared on “Larry King Live,” guest-hosted by Jimmy Kimmel. Kimmel laid into her for the site’s Gawker Stalker map, which charted celebrities’ locations in NYC, and predicted her descent into hell. (Sicha has referred to Gawker Stalker as “the bane of my existence.”)

In October 2007, then-feature writer Vanessa Grigoriadis wrote a damning article for New York magazine about Gawker. She described her pain at reading Gawker’s excoriation of her Times Vows column the day after her wedding, calling the site a “foul, bloggy sewer.” Around the same time, Gawker started an unpopular new compensation system in which a writer’s payment depended on pageviews. In December 2007, Sicha, Gould and a third Gawker editor simultaneously quit.

Over time, Gould’s professional relationship with Sicha grew into a friendship, although what seems to be a complicated one. The two have continued on in different parts of the media industry — Sicha in managerial roles, Gould as a novelist, book publisher, and marquee contributor to publications like The Cut and Bookforum. Sicha has successfully navigated the internal politics of the Times, which requires a certain amount of schmoozing, but he does not tend toward self-exposure. He doesn’t often publish his own writing and his one book was a slim creative-nonfiction portrayal of financial-crisis era New York City. He has settled into his role as the man behind the curtain, following up on his years pulling the strings of digital media.

“Working at Gawker, depending on how you look at it, was either the thing that gave me a career in the first place and enabled me to be a writer, full-stop, or it was the most traumatic thing that ever happened to me and was crippling and painful and shaped my personality and career in ways that I’m much worse off for,” Gould told me. “Both of those things are true simultaneously,” she continued. “I think I would be selling [Sicha] short, and underestimating his intelligence and his intentionality, if I didn’t somewhat hold him responsible for those things.”

After his two stints at Gawker and then a role at the ill-fated Radar magazine, Sicha and his colleague of Gawker and Radar Alex Balk branched out on their own in 2009. The pair founded The Awl — first a standalone blog, then a blog network. The Awl embodied post-financial crisis digital media; it was a blogger’s blog. It became, as Widdicombe put it, a great “critical, if not financial success.” The wider network included The Hairpin, a beloved blog focusing on women, and Splitsider, a comedy blog, among others. The Awl network’s editors were tastemakers, and built the reputations of new writers by allowing them to flex their creative muscles.

“One of the reasons that so many writers came through The Awl was that it gave people a chance to be themselves,” says Tom Scocca, the current politics editor for Slate who worked with Sicha at The New York Observer. “Choire has a real gift for getting people to come across as themselves, which is a sort of remarkable trait to have brought to an institution like the Times.” Awl network contributors and editors went on to influential corners of the media industry — including the Times — but digital advertising was still a fickle model. After an ill-fated deal with Medium and a subsequent re-pivot, The Awl shut down for good in 2018. Once again Sicha landed on his feet. As he was moving away from The Awl, he took a job as the partnerships manager at Vox Media, working with clients like Facebook and Apple on content creation and distribution via new channels. While perhaps uninspiring, this interlude might have given him the skills to navigate a much larger institution.

The Times Style section editor is a role Widdicombe called “one of the absolute plum jobs in New York City journalism.” And in 2017, the Times hired Sicha to succeed its previous editor of the section, Stuart Emmrich, who helmed Style starting in 2010 before departing for the Lifestyle section at the Los Angeles Times. (Emmrich then moved to editing Vogue’s website, where he learned how to use a CMS, and recently left.)

Critique and mockery of the media establishment, its egos and its hypocrisies, was a through-line in Sicha’s previous roles. Yet he has ridden those tenures straight to the core of the industry. His path showed that a journalist — a white, male one, at least — can, throughout his career, gently rib The Establishment and not be blackballed. In fact, he could be rewarded for it.

Sicha’s resume isn’t the only unorthodox aspect of his ascendance. One does not simply stumble into the position of section editor at the New York Times, yet his demeanor suggests that he’s just not taking this all too seriously. For example, he began our interview by joking, “I’m prepared to be cancelled! Let’s do this.” He mentions often in interviews that he disdains authority figures and shares that during his brokest years, he searched couch cushions for money. His blunt emails deploy CAPS-LOCK and exclamation points liberally. (“lol can you believe i ignored you,” begins one Style section rejection shared with  me.) There’s even a rumor that Sicha asked Twitter to remove his verified blue check mark. For the record: “I have never been verified on Twitter and have never had a blue check mark. I love that rumor.” When I asked Sicha for his age at the end of our talk, he looked it up on Wikipedia.

Sicha’s I’m-still-one-of-you posture toward the media’s lower echelons of younger editors and freelance writers has made him overwhelmingly well-liked (or at least approved of) in a notoriously bitchy, sniping industry. He has garnered not just goodwill but respect among his writers and peers. (Jeff Koyen, the former editor of New York Press who listed Sicha as one of “The 50 Most Loathsome New Yorkers” in 2004, called him a “superior editor” in a recent email.) Several of Sicha’s past colleagues who declined to be interviewed for this article still made a point to note that they love him or find him to be brilliant.

In practical terms, Sicha is unusually hands-off for an editor. He isn’t guided by an “idea of what an imaginary reader wants,” said Scocca, explaining that Sicha’s encouragement of the pursuit of strange ideas and passion projects “gives writers and pieces the strongest opportunity to stand or fall on their own terms.” Scocca, for example, wrote daily weather reviews for The Awl. Not weather reports — weather reviews. They became one of the site’s trademarks.

In 2014, The Awl published a feature, prophetically, about the history of the Times’s Style section itself. The writer, Jacqui Shine, a trained historian, said Sicha greenlit the original assignment at 2,500 words. But as the scope and length widened throughout her research, Sicha encouraged her to keep going. The published piece is an incredible 12,000 words long. After publication, Shine said other editors reached out to her, expressing the wish that she’d pitched the story to them first. “They wouldn’t have taken it!” She said. “[Sicha] was able to tolerate not knowing what the final shape was going to be. As a writer, that’s hugely flattering.”

This view was echoed by Katherine Rosman, a features reporter for Times Style. “My sense is he assumes that you are good at your job and that you are in the position that you’re in for a reason,” she said. Not meddling with talent and not diluting great ideas by committee are two smart strategies in a creative workplace that are rarely deployed successfully.

Still, there may be a psychological element to Sicha’s latitude: in an email, he wrote to me that it is his nature to be “people-pleasing.” “He does have a problem saying ‘no’ clearly,” said Widdicombe, who wrote a social column for Style until recently (he is now the editor-in-chief of Avenue, a luxury magazine). “Sometimes you’ll have an email exchange with him, which might lead you to believe the answer will be ‘yes’ in the future. In fact, it’s really ‘no’ and he just doesn’t say that.” He described his friend of nearly 20 years as “conflict averse.”

Perhaps not surprisingly, Sicha chafes at the actual process of managing. When he quit Gawker for the second time in 2007, he told the New York Times, “I’ve completely lost my taste for management.” Plenty of editors dislike it. But they don’t necessarily share this view publicly with the Times — and later get hired by the Times in a management role.

There’s a candor and a self-effacement to Sicha not often seen in editors of his professional stature. He distrusts the myth of the single visionary. After our call, he sent me a long email explaining why it is the Style section’s other editors, writers, and designers who do the real work. “I don’t really … do anything,” Sicha wrote, continuing:

“[I]f your central question is ‘Gosh how does Choire Sicha make the Style section so magical?’ Then the answer is … I do not. It’s not me doing any of it! I don’t write the stories, I don’t assign the stories, I don’t design the stories, I don’t take the photographs, I don’t edit the stories. Man, I don’t even do the INSTAGRAM stories. 

And this can sometimes be really annoying or stressful for folks here! When things are a mess, I’ll let them be a mess until someone decides to clean it up. It can be uncomfortable, or awful. I spend a lot of time working in the backyard since I live kinda in nowhere and I think a lot about permaculture and letting plants and animals find their niches. Sometimes you have to wait a few seasons to see what happens and where something wants to be. Like most plants and people, I find my way slowly and have to fail a bunch. How can you succeed if you don’t have room to try something and fuck it up? It doesn’t help to have someone constantly telling you how to do things! You’ll figure it out later! (Can you tell I hated high school.)

It’s possible that I’m like a landlord; I am an unnecessary interloper who only extracts value and rarely gives it.”

Lifestyle journalism is typically thought of as “soft news,” as opposed to “hard news” subjects like politics or business. This reputation is hard to shake, despite the fact that lifestyle writers and editors need to be well-versed in both of those subjects, as well as history, sociology, and culture, in order to do their jobs.

The Times Style section is likely the most prestigious in the country, but still has had to fight for respect. The best way to understand the origins of the Style section is to read Shine’s piece for The Awl. But the (very) abbreviated version is this: Throughout the 20th century, oftentimes the only place where a female reporter or editor could find work was in a newspaper’s “women’s pages,” which, in time, melded with “society pages” and became modern-day style sections. “Women’s pages” typically covered “The Four Fs” — food, fashion, family, and furnishings — and were deemed less important than other areas of journalism. Stories that appear in Style get “ignored and trivialized,” Shine said, even when they cover the same subjects as other sections in a newspaper.

Style can be broadly viewed as coverage of how we live our lives. The question is,  whose lives? Shopping purchases, food choices, and parenting experiences vary widely based on race, gender, and class privilege. Given that newspapers, including the Times, are funded by advertising and have an incentive to attract wealthy subscribers who luxury brands then pay to be seen by, it’s not surprising that Style coverage has historically courted populations with abundant disposable income.

While reportage about wealth and privilege is a valid subject in its own right, there is a tricky balancing act at play. Is Style meant to be aspirational for its readers, presenting a glossy image, or is it a more subtle critique of its readers, through articles about “stress-shopping” for jewelry? So often, this answer is ambiguous. It depends on how you’re reading it: the politics are often smuggled in through subjects that might seem frivolous.

Adding to the ambiguity — a calcification of the What Is This Section, Even? that Sicha himself invoked — is Style’s history of, well, silly trend pieces. For example, 2008 articles delivered the breaking news that single, straight men have pet cats and that women wear dresses. In 2012, man buns got a dedicated article; a 2014 piece delivered the news that teens were staying up all night texting, something the paper termed “vamping.” These types of trend pieces provoked mockery on Gawker and elsewhere;’s media critic Jack Shafer dedicated several columns to what he called the “Bogus Trend of the Week.” As Gould put it, “It was always unclear … whether this was a knowing troll on the part of the Times or whether it was the Style section’s raison d’etre.”

Readers’ increased ability to critique the media, thanks to social media generally and Media Twitter in particular, is partly responsible for changing coverage. “Lifestyle journalism, like every type of journalism, has had to rethink itself in the world where readers can and do talk back,” said Rosman, who has been a Style reporter since 2014. “And I think that there is nothing more enjoyable for the internet than finding a New York Times Style section story to make fun of.” The mantle of being The Newspaper Of Record exacerbates this critique. “You could do the monocle story elsewhere and it would be like a dumb story that nobody would read or people would roll their eyes at or whatever,” she noted. “But you do it in the Times and it’s a whole thing.” Sicha does not seem content for Style to stay in its pre-established lane, or double-down on the trendpiece legacy. “[He] definitely has allowed me to do stories that represent a broad philosophy of what a quote-unquote lifestyle section can be,” said Rosman, noting that “Style previously had a much more narrow purview.”

Style increasingly publishes articles that could have been assignments for the politics or national news desks. Its coverage of social justice issues has been particularly strong. In May, it ran a piece about a democratic socialist candidate in Philadelphia running for State Senate (who also happened to have been an editor at the storied journal n+1). Last year, Shine had a piece in Style about gun culture in Iowa. A fashion package included an article profiling garment workers in Pakistan, Indonesia, Cambodia and other countries.

Sicha has also established a de-facto Internet Desk with a crew of youngish writers and designers. Taylor Lorenz, formerly of The Atlantic, covers internet culture with an eye to social media as a universe unto itself. John Herrman, a former co-editor of The Awl who previously wrote for the Times Business section, has covered technology for Style. And Caity Weaver, formerly of GQ and Gawker, doesn’t really cover anything, which is to say her beat comprises Dunkaroos, glitter and Pamela Anderson.

The section also looks more like the internet with the contributions of designer and art director Tracy Ma, who came to Style via Businessweek, where she refined a digital-Baroque sensibility. Ma has turned articles into interactive experiences, melding lo-fi vibes, as in a Y2K feature, with high-production absurdist GIFs, like rats bouncing around in a car. The high point of Style innovation might have been the artist and author Jenny Odell’s 2018 “A Business with No End,” a surreal exploration of ecommerce supply chains.

Sicha has managed to widen the scope of Style without making it the junk drawer of the Times. Style is a place where experiments can be run and boundaries pushed. This is likely possible because Style is still seen as a less fraught area of the newsroom than, say, the Politics desk (not to mention Op-ed). But Sicha was also up front about his expansive outlook in a Times Q&A upon his hiring: “I have a hard time imagining anything beyond the purview of Style,” he said.

That doesn’t mean all readers understand or appreciate the evolution. When Widdicombe wrote his society column at Style, he said “the older guard would often complain to me that they didn’t understand what had happened to the Style section … [T]hey wanted the Style section to cover couture week in Paris” — the old stuff like hemlines and shoes. “They didn’t understand why Taylor Lorenz was writing about what 17-year-olds are doing on TikTok,” he said. The answer seems pretty simple: It’s a subject that many, many people care about now, and, frankly, should care about. The vanguard has always found a home in the Style section; the vanguard is just changing.

The Style section today is unrecognizable to the one I began reading during high school in the late 1990s and early 2000s. During that era, Style embodied the “Sex & the City” fantasy version of New York City: a world of velvet ropes, designer clothes, and weekends in the Hamptons. The section encouraged — or maybe preyed on — aspirations for status and consumption. Today, Style instead resembles a smartly curated social media feed. The section is not bereft of pretty objects and pretty people; there will always be an appetite for a gorgeous actress’s killer beauty regimen. But the section is both wittier and more self-aware and the aspirations it encourages are wider, grander than monetary success: Racial justice; a world free of sexual abuse; dignity, parity, and joy. It’s less rich, less white, less elitist, and more fun, which helps right now.

As the editor of Style at this moment in history, Sicha said he is cognizant “that every one of us has some varying level of crisis in their life, whether it’s new or old or newly terrible.” That largely means avoiding pieces that could be regarded as tone deaf or full-on hate-reads. (Under earlier iterations of Style, the infamous April article about honeymooners trapped in the Maldives might have leaned even more into hate-read territory.) “We’re being a little bit more respectful than we normally would be because we know that people who are reading the New York Times have families who are sick, or are doing childcare while working, or are dealing with Zoom funerals — which is a terrible, terrible phrase,” Sicha said. “So, I do like pissing people off and we’ve definitely done a little bit in the last couple of months. But it’s just a time to be a little more empathetic to people.”

Foremost among Sicha’s qualities that make him optimal for the moment is his elasticity. “It’s very difficult up close to understand the times in which we’re living right now,” he told me. “We’re trying diligently to do that night and day, in different methods. And we don’t always succeed or we don’t always succeed fully, but we’re trying.”

Trying certainly counts for something. Mainstream journalism, and the Times in particular, has long suffered a reputation of being elitist and out-of-touch. But Style addresses contemporary culture and society, and thus must pay attention to changing times. Someone with Sicha’s deep understanding of the media industry must also know that changing the direction of the ship — especially a craggy old behemoth like the Times — occurs slowly. But in three years, Sicha has shown that change at the scale of a section is possible. Style is without question the most interesting, thought-provoking, and inclusive — that is to say the best — section at the Times right now, and likely suggests where the rest of the publication is headed.

Sicha has become something of an elder statesman, running his own show at the most powerful publication in the world. Does that mean that he’s now a company man, happily molding his own fiefdom? Or might he set his sights higher someday as an iconic New York City editor-in-chief along the lines of Tina Brown, David Remnick, or Adam Moss? Do those jobs even exist anymore anyway?

The very top job doesn’t seem like Sicha’s temperament. In all his roles past and present, he’s more like an editorial jester, the wisest Shakespearean archetype: He entertains us with slight satire, but also educates us about ourselves. The Style section might do its fair share of trolling, but the kind of trolling it does under its new editor is not about punching down, disenfranchising anyone, or making abstruse arguments about the nature of speech. It’s about expanding the conversation to encompass as many voices and subjects as possible, thus broadening the Style’s relevance beyond its traditional wealthy audience. Rather than developing editorial in his own image, Sicha is once again allowing everyone to be themselves, no matter the label.

Our conversation turned to Twitter, as most media conversations eventually do. In her resignation from the opinion section in July, Bari Weiss complained that the social network functions as the new editor of the Times. Sicha isn’t sure Twitter actually causes much systemic change, but it’s certainly a ceaseless engine of inspiration for covering whatever’s happening right now. “I’m pro-the people causing trouble” on Twitter, Sicha said. “I’m on their side.” He added in a teasing voice, “More trouble! That’s my motto!”

CORRECTION: Stuart Emmrich edited NYT Style beginning in 2010, not for 17 years.

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