In recent years, it’s become harder to tell whether fashion can still stand on its own, without leaning on the scaffolding of sport, film, or whatever cultural tentpole happens to be in rotation. But with the sustained relevance of System and the sharp ambition behind its latest expansion, Editor-in-Chief Jonathan Wingfield offers a clear answer: yes—fashion can still trade on itself.

It is a business, unquestionably—but a beautifully complex one, in constant dialogue with culture. And in that dialogue, the currency of creativity proves more stable than gold. Unlike so many aspects of contemporary life, its role is inimitable, its value evergreen.

In this conversation, Wingfield traces his own route—from suburban teenage boredom and record sleeves to the visual literacy that would come to define his work. We talk about System’s origins, the logic behind System Collections, and what gets lost when coverage is dictated by algorithms rather than curiosity.

“The most interesting commentary on a film often came from the costume designer, not the star. That logic applies to fashion too.” - Jonathan Wingfield

Episode Highlights:

From suburban boredom to fashion curiosity - Wingfield traces his creative awakening to the disconnect between small-town life and the cultural energy of nearby London—music, record sleeves, and magazines were his early portals.
The record sleeve as first editorial influence - A Peter Saville–designed cover for New Order’s True Faith becomes an entry point into the world of typography, photography, and image-making.
A formative mentorship on the road - A months-long carpool with UK publishing legend Alan Lewis becomes a crash course in magazine craft—headline writing, storytelling, and editorial voice.
Why editing is about the final decisions - For Wingfield, the joy of putting a magazine together isn’t in the interviews—it’s in the final details: captions, pull quotes, and headlines that shape meaning.
System’s founding as a response to access fatigue - Frustrated by increasingly hollow interviews with celebrities, Wingfield wanted a space for deeper, more sustained conversations—System was his answer.
Virgil Abloh as a cultural inflection point - A cover story featuring Virgil becomes a turning point for System, bridging industry credibility and outsider influence, and reframing who the magazine is for.
The slow reveal: System’s relationship to time - Wingfield shares why the magazine resists real-time commentary and favors longer arcs—interviewing designers after the noise has died down.
The launch of System Collections - He introduces System’s newest project: a seasonal, time-capsule-style publication that offers deep visual and editorial takes on fashion month.
On interviewing well—and waiting for silence - One of his top tips: don’t rush to fill silences. Real answers often follow the pause.
What’s contemporary now? Swerve the algorithm - Wingfield’s closing reflection: avoid being trapped in feedback loops. Discovery, intuition, and counterintuitive creativity are what truly move culture forward.

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Editing Creative Culture with System Magazine’s Jonathan Wingfield 40:11 Share

What's Contemporary Now?

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Editing Creative Culture with System Magazine’s Jonathan Wingfield