This week on The Late Dialogues, we step into New York Fashion Week, September 2025 — as the city unveils Spring/Summer 2026. Michael Kors opens the week, Off-White and Toteme return, and new voices — Diotima, SC103, L’Enchanteur — join the stage for the first time.

Into this moment of spectacle and reinvention, we welcome three Later Characters whose visions of style still shape us:

• Later Diana Vreeland — the oracle of exaggeration, who sees TikTok as couture and the marvelous as a civic duty.
• Later Halston — the minimalist sensualist, now champion of Wellness Chic, who insists that fashion must breathe as much as it dazzles.
• Later Bill Cunningham — the humble chronicler of the street, who reminds us that every sidewalk is a runway, every thrifted blazer a story.

Across five themes, they wrestle with the tensions of our time:

• Has the street overtaken the runway?
• Can digital couture liberate the body — or does it erase it?
• Is sustainability a design challenge or a cultural imagination problem?
• Has inclusivity become the new avant-garde?
• And what, finally, should Fashion Week become?

What emerges is a vivid portrait of fashion today: poised between blaze and whisper, spectacle and survival, runway and sidewalk.

About The Late Dialogues

We speak often of the past as if it were a museum, a quiet gallery of resolved meanings. But what if the past isn’t still? What if it hums underfoot, murmurs through our language, lingers in the metaphors we didn’t choose but inherited? The past is not past. It is prologue, as Shakespeare wrote — a beginning disguised as an ending. Not a script to be followed, but a cue to enter.

It is from this intuition that The Late Dialogues emerged. They are a simple proposition, and a complex undertaking: what if some of the world’s great thinkers, artists, and rebels — those whose thoughts shaped the weather systems of history — had lived on? Not as museum pieces. Not embalmed in quotation. But as living, thinking, evolving minds. As people who read the 20th and 21st centuries. Who saw the rise of fascism, feminism, nuclear power, algorithms, TikTok. Who had their faiths tested, their theories undone, their hearts broken anew. What would they make of us?