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Taylor Swift Asks Anna Wintour 8 Questions | Go Ask Anna | Vogue

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Vogue hands the microphone to its biggest cover star yet — and lets her interrogate the boss.

On August 8, 2019, Vogue dropped a special edition of its long-running web series “Go Ask Anna,” and this time the questions didn’t come from strangers on the street. Taylor Swift, freshly announced as the cover star of Vogue’s September 2019 issue, sat down to grill editor-in-chief Anna Wintour directly. The result is an eight-minute-ish flip of a format Vogue has run for years, mixing live-action footage with illustrated flourishes.

• Swift, just named the cover star of Vogue’s September 2019 issue, takes over the “Go Ask Anna” format and puts eight specific questions to Anna Wintour.
• The episode was directed and illustrated by Todd Selby (The Selby), produced by Camilla Ferenczi, and styled by fashion editor Taylor Angino.
• Swift’s questions cover Wintour’s tenure running Vogue, the trends that defined her career, and her advice for navigating the fashion industry.

A Role Reversal for a Familiar Format

“Go Ask Anna” normally works one way: pedestrians and Vogue readers lob questions at Wintour on camera, and she answers with her usual clipped efficiency. This installment inverts that setup entirely. Swift, riding the momentum of her September cover announcement, becomes the interviewer, and Wintour becomes the subject fielding a celebrity’s curiosity instead of a stranger’s.

That switch matters because of who’s asking. Swift isn’t a passerby with a passing interest in fashion — she’s the face Vogue chose to headline its most consequential issue of the year, the September book that traditionally sets the industry’s tone heading into fall. Handing her the floor turns a recurring web segment into a promotional centerpiece for that cover.

The Eight Questions

Swift’s line of questioning zeroes in on Wintour’s decades at the top of Vogue: what philosophies have guided her editorial decisions, which trends she considers genuinely defining, and what advice she’d give someone trying to survive in an industry as unforgiving as fashion. Wintour, known for rarely elaborating in public settings, offers her take on the notable shifts she’s watched ripple through fashion during her run at the magazine.

Eight questions, one sitting — pop’s biggest name pressing fashion’s most powerful editor for the trends and philosophies that actually stuck.

The format keeps things brisk and conversational rather than combative, which fits the tone Vogue has cultivated for the series since it launched. Swift’s presence, though, raises the stakes of what’s otherwise a lighthearted bit — this is the artist whose musical reinventions have made her something of a case study in how public figures evolve their image over time, asking the person whose editorial calls have shaped fashion’s biggest names for years.

The Team Behind the Camera

Beyond Swift and Wintour, the episode leans on a specific crew to pull off its blend of live footage and animation. Todd Selby, working under his The Selby banner, directed and illustrated the piece. Camilla Ferenczi produced it, with Taylor Angino handling styling. Zach Eisen shot the cinematography, Linda Wu worked as assistant camera, Gautam Kadian served as gaffer, Phil Shipman handled sound recording, and Michel Sayegh built out the animation woven throughout.

That combination — Selby’s whimsical illustration style layered over straightforward interview footage — is what separates this episode visually from a standard magazine sit-down. It’s closer to a hybrid of fashion editorial and animated short than a typical talking-head video, and it’s part of why Vogue chose this format rather than a straight profile piece to mark Swift’s cover announcement.

Strategic Timing for Market Entry

Vogue doesn’t hand its September cover to just anyone. The issue is the industry’s biggest of the year, the one advertisers and designers treat as a bellwether, and pairing that announcement with a Wintour interview conducted by the cover star herself is a deliberate piece of rollout strategy. It gives Swift’s fans a reason to watch a Vogue web series they might otherwise skip, while giving Vogue a fresh angle on a format it’s run dozens of times with anonymous questioners.

The episode landed the same week Swift’s September cover news broke, which is no accident — Vogue timed the release to ride the attention already building around that announcement, using Swift’s own curiosity about Wintour’s tenure as the hook to keep people watching past the cover reveal itself.