From Bank Job to Bill Cunningham's Role: How Simbarashe Cha Became the New York Times Fashion Photographer

Simbarashe Cha went from pursuing music for 15 years to working in banking for a decade before buying his first camera at 32, eventually becoming the New York Times style columnist by focusing on practice, admitting his blind spots, and staying obsessed with making relatable, accessible fashion photography.

Summary of Simbarashe Cha on 10,000 Hours of Street Style Photography. Every timestamp links into the original audio.

The short version

• 00:01:53 — He didn’t purchase his first camera until age 32, after spending his twenties pursuing music and his thirties working in finance
• 00:12:19 — Working at a camera reseller in Brooklyn sparked the realization he needed a creative hobby to fill the void left by abandoning music
• 00:21:49 — He realized his eye was more stylistically discriminant than other photographers like Brandon Stanton, which led him to consciously seek out more fashionable-looking people and eventually transition into fashion photography
• 00:27:00 — Watching a Bill Cunningham documentary forced him to confront how he had neglected his ex-partner’s interests, leading to a profound reckoning about his own blind spots and accountability
• 00:32:16 — After the Bill Cunningham realization, he set a concrete goal to become good enough to be on the shortlist for succeeding Cunningham’s column at the Times
• 00:33:20 — He calculated it would take six and a half years to achieve 10,000 hours of mastery by combining the principles of putting in reps and practice-makes-permanent
• 00:46:22 — During COVID lockdown protests in 2020, a New York Times photo editor called him while he was heading to a protest after seeing his Instagram stories, launching his photojournalism career
• 00:54:16 — Even now, he reminds himself every morning while brushing his teeth that his current job as a New York Times style columnist still feels surreal and incredible
• 00:58:46 — His core mission has always been photographing people whose personal style feels accessible and within reach for viewers, rather than showcasing only extreme or unattainable fashion

In depth

A career built on wrong turns, not a plan

What’s striking about Simbarashe Cha’s path to the New York Times is how little of it was deliberate. He spent his twenties chasing a music career with no backup plan, worked a day job in banking that he fell into almost by accident after running out of money on a road trip, and didn’t own a camera until he was 32 00:14:21. Even the camera purchase wasn’t a creative epiphany — he bought it because he worked at a camera reseller in Brooklyn and felt it was strange not to own one himself, and because he needed something to fill the hole left by quietly abandoning music 00:14:03.

The through-line he offers, in hindsight, isn’t talent or vision but restlessness combined with a refusal to settle into routine work, even while he was doing routine work for nearly a decade 00:07:39. He frames the banking years not as a detour but as unexpectedly useful training — learning to read people’s financial lives taught him things about human behavior that later served him when he started his own photography business 00:12:13. The lesson he draws is modest and a little uncomfortable: careers built on wandering can still arrive somewhere coherent, but only in retrospect. At the time, none of it felt like a plan.

Discovering an eye by watching someone else’s

The pivot from hobbyist street photographer to fashion photographer didn’t come from studying fashion — it came from walking alongside Humans of New York creator Brandon Stanton in the early days of that project, before Stanton had any real following 00:19:59. Cha noticed that Stanton would stop literally anyone, regardless of how they looked or what they wore, if he found something interesting in them 00:21:13. Watching that indiscriminate curiosity forced Cha to confront something about himself: his own eye was, in his word, prejudiced — he was instinctively drawn to people with a certain stylized look, not everyone 00:22:00.

This is a genuinely unresolved tension he doesn’t fully smooth over: he’s careful to say this isn’t a value judgment on Stanton’s approach, which he clearly admires, but an honest admission that his own sensibility pulled him somewhere narrower 00:22:09. Rather than fight that instinct, he leaned into it, and that self-diagnosis is what turned a general street-photography habit into a fashion-specific one — he started hunting for more stylish subjects, which in turn pushed his blog from a technical photography journal into something closer to a fashion publication 00:22:24. It’s a useful case of a career direction emerging not from ambition but from paying attention to a discomfort with someone else’s method.

The Bill Cunningham documentary as a personal reckoning

The most emotionally loaded moment in the conversation is Cha’s account of watching the Bill Cunningham documentary on Netflix, not for professional inspiration but almost by accident, at the suggestion of someone he’d photographed 00:26:27. Partway through, he realized the narrator’s voice was naggingly familiar — and then placed it: it was the same voice his ex-partner used to tune into religiously on Sunday mornings while he sat in the next room watching sports, uninterested 00:26:52. That recognition triggered something larger than nostalgia. He describes realizing, in real time, that he had a blind spot he’d never admitted to himself: a carelessness toward the relationship, not through conflict but through simple inattention to what she cared about 00:27:28.

What makes this worth dwelling on is the self-criticism he volunteers unprompted — he notes that almost everyone he knows narrates failed relationships as either mutual drift or the other person’s fault, and that he had always told himself the same story, until this moment forced him to admit the breakdown had been partly his own doing 00:24:39. He frames this not as wallowing but as functional: the discomfort of that realization is what he credits with supplying the discipline for everything that followed, because it reframed failure as something within his control rather than circumstantial 00:29:30. He even called his ex immediately after finishing the documentary to acknowledge it 00:29:11 — a detail that underlines how raw and immediate the reckoning was, not a tidy story reconstructed after the fact for an interview.

From that same viewing came the professional spark: watching an eighty-something Cunningham radiate uncomplicated happiness in his work, more than any musician Cha had idolized, planted the question of whether photography could sustain that kind of satisfaction for him too 00:28:19. The emotional and professional revelations are tangled together in his telling — he doesn’t separate them, and that’s arguably the point: the same moment that exposed a personal failing also supplied the motivation to work differently going forward.

Turning a vague goal into a hard number

The ambition that came out of the Cunningham documentary was deliberately unglamorous: not to get the column, but to be good enough that his name might plausibly appear on a shortlist whenever Cunningham eventually stepped back 00:32:16. Cha is explicit that even this was aspirational in a bounded way — he wasn’t claiming he’d get the job, just that he wanted his skill level to be defensible if the conversation ever happened.

To make that goal operational, he leaned on Malcolm Gladwell’s popularized claim about 10,000 hours of practice producing mastery, and ran the arithmetic against how much time he was realistically able to spend shooting on the street each week, landing on roughly six and a half years to hit that threshold 00:34:17. He explicitly measured that number against his failed decade-plus attempt at a music career, reasoning that if he could commit to something even half as long and shoot with real discipline, he could outperform what fifteen years of unfocused musical effort had produced 00:34:29.

The other piece he credits, alongside sheer repetition, is a phrase borrowed from a former banking colleague — that practice makes permanent rather than perfect — which pushed him to treat early rejections from subjects not as discouragement but as diagnostic data about what in his approach needed adjusting 00:37:26. This is a meaningful distinction from simple grinding: the claim isn’t just that volume of practice matters, but that mindless repetition locks in whatever habits you already have, good or bad, so deliberate correction has to run alongside the hours. He’s careful to note this was never a plan to become a professional photographer outright — mastery was the stated goal, not a career 00:34:08, and the career only crystallized later, almost as a byproduct.

From protest photography to an accidental column, and what ‘accessible style’ means to him

The actual route to the Times had little to do with the Cunningham goal by the time it happened — Cha says that by the pandemic he’d essentially forgotten about it 00:44:36. What reopened the door was COVID shutting down nearly all paid photography work, which pushed him to consider photojournalism for the first time, and then the George Floyd and Breonna Taylor protests, which he began covering on his own initiative and posting to Instagram stories, content designed to vanish within 24 hours 00:45:54. A Times photo editor reached out directly after seeing those stories, launching a six-month stretch shooting demonstrations between New York and Washington 00:46:34.

He draws a direct line between his protest photography and his fashion philosophy: rather than chasing images of anger or conflict, which he says were easy to find and in demand from other outlets, he deliberately sought out hopeful faces and expressions of solidarity, because that was consistent with a portraiture instinct he’d already built — making a viewer want to be inside the frame rather than observing it from a distance 00:48:04. He credits that consistency of approach, more than any single image, with why the Times editor who hired him seemed to understand his sensibility immediately 00:49:03.

The writing side of his current role, notably, wasn’t assigned to him either — he talked his way into it after a Milan Fashion Week shoot ran without its planned text because an editor was too busy to write the introduction, and he volunteered, pointing out that his blog had always been as much writing as photography 00:55:09. That same accidental, cause-and-effect pattern — a vacancy, a volunteer, a role that sticks — repeats throughout his account of how he ended up with the Look of the Week column. Through all of it, he returns to one stated principle that hasn’t shifted: his interest has never been in spectacular or unattainable fashion, but in subjects whose style reads as something an ordinary viewer could plausibly attempt themselves 00:58:46, a standard he applies whether he’s shooting in Tokyo, London, or, by his own admission, hasn’t yet tried in Montreal.

Summarised automatically. Listen to the original for the full conversation — this is not a substitute for it.