Dear Readers,
This week we release a special episode of The Late Dialogues that steps directly into the theater of New York Fashion Week. September 2025 — the moment the city unveils its Spring/Summer 2026 collections. Michael Kors opens the week, Off-White and Toteme return with force, and new voices — Diotima, SC103, L’Enchanteur — bring fresh textures, identities, and imaginations to the runway.
Into this swirl of spectacle and reinvention, we welcome three Later Characters:
- Later Diana Vreeland — still the oracle of exaggeration. She calls Instagram and TikTok the new salons, where style performs itself in fifteen seconds. For her, fashion’s highest duty remains to astonish.
- Later Halston — the sensual minimalist re-forged as a prophet of Wellness Chic. He argues for longevity, fluidity, and simplicity as the true avant-garde in an era drowning in noise.
- Later Bill Cunningham — the chronicler of the street, who still pedals the city in spirit. For him, every sidewalk is democratic, every thrifted blazer a small rebellion against disposability.
Across the episode, they wrestle with five urgencies:
- The City as Runway — Has the street overtaken the tent, and is democracy itself the new avant-garde?
- Technology, Couture, and the Body — Can AR try-ons, AI models, and digital couture liberate us — or do they risk erasing the body itself?
- Sustainability vs. Spectacle — Can glamour and survival coexist when every gown casts a shadow?
- Diversity and the New Avant-Garde — Is inclusivity radical, or has it become another costume on the stage?
- The Future of Fashion Week — Should NYFW remain a blaze of theater, evolve into fewer, deeper shows, or dissolve into the everyday spectacle of the city?
What emerges is not a consensus but a choreography of tension: between blaze and whisper, spectacle and restraint, the feed and the street. The conversation leaves us with the haunting possibility that New York itself — its sidewalks, its scrolls, its sudden gusts of wind — may be the true designer of our time.
That is the experiment of The Late Dialogues: to let influential voices return, evolve, and take a stand in the urgencies of our moment. Fashion is one of those urgencies — as much about identity and democracy as about fabric and cut.
We hope you’ll listen, argue along, and carry these voices with you as Fashion Week unfolds.
Until next time — keep the conversation alive.
FULL SCRIPT BELOW
Introduction
DAVID:
Welcome to The Late Dialogues — an exercise in generative fiction, a space where voices from the past return to reflect on the urgencies of the present.
Through the ether of thought, and with respectful assistance from AI, we’ve rekindled the spirits of three historical minds. Not as they once were, but as they might now be — shaped by all that has unfolded since their time on Earth.
These are not the original speakers. They are Later Characters — speculative continuations of thinkers who left behind questions still unresolved. They have read what came after. They have changed. They carry new ideas, new wounds, new doubts.
They are not the persons they once were or the towering intellectual figures they have become, they are less and more than that, but tonight, they speak.
And tonight, they speak into the very heart of New York in September 2025 — a city that once again thrums with the theater of Fashion Week. Michael Kors prepares to open the week, Off-White and Toteme return to the schedule, and new voices—Diotima, SC103, L’Enchanteur—prepare their debuts. The air is heavy with gingham and lace from the summer just passed, with anticipation of what will shimmer next season. It is here, amid spectacle and reinvention, that I welcome three voices whose sensibilities still shape our understanding of style.
First, Diana Vreeland — the oracle of style, who once transformed Vogue into a stage for the marvelous. In her Later life, she has embraced the Digital Salon: TikTok as couture, Instagram as the new editorial, AI as a tool for exaggeration rather than correctness. She comes to remind us that “the marvelous is a civic duty,” and to ask whether Fashion Week still has the courage to exaggerate.
Next, Halston — the minimalist sensualist. In his lifetime, he draped Studio 54 in fluid silhouettes and American ease. In his Later incarnation, he has evolved into a prophet of Wellness Chic: sustainable fabrics, genderless silhouettes, clothes that liberate rather than cage. Tonight, he joins us to ask whether purity of form can survive the noise of spectacle.
And finally, Bill Cunningham — the gentle chronicler of the street. The man who once pedaled through Manhattan capturing unposed marvels, who saw sidewalks as the truest runways. In his Later life, he embraces Instagram grids and TikTok feeds as digital sidewalks, but still insists that “fashion is the armor to survive the everyday.” He is here to remind us of democracy in style — that what people wear between shows often tells us more than the shows themselves.
Theme 1: The City as Runway
DAVID:
As we sit here in New York in September 2025, the city itself seems to throb with its own runway. This summer, gingham spilled from boardwalks to midtown, lace traced the outlines of dresses on subway platforms, and oversized shirts were worn with a kind of lazy luxury that felt both careless and exacting. Now Fashion Week arrives, September 11 through 16, and inside the official tents Michael Kors will open the week, while Off-White, Toteme, and fresh names like SC103 and Diotima prepare to show.
I wonder — does the city still borrow its style from the runway? Or have the streets become the truer stage, with Fashion Week now a mirror of what has already walked past us?
⸻
VREELAND:
Darling, the street has always been a stage. But a stage needs direction, needs exaggeration! I don’t want to see gingham as if it were a picnic cloth, I want gingham the size of a building, gingham reimagined in hologram and projected across Times Square. Otherwise, what’s the point? Fashion Week must give us a vision larger than our feeds. If I wanted to see reality, I’d look out the window — not at a runway. The marvelous must be taller than the skyscrapers.
⸻
HALSTON:
And yet, Diana, the power of gingham this summer was not its exaggeration, but its ease. A slip-on short, a loose top, carried from brunch to the office without effort. That is where style lives now — in the freedom to move. If Fashion Week pretends it leads, but does not learn from the comfort people already wear, it risks becoming irrelevant noise.
⸻
CUNNINGHAM:
I have to agree. Walking here today I must have seen fifty versions of those Sandy Liang sets. Not copies, not imitations, but variations — layered with silk scarves, paired with sneakers, worn with blazers. The street is alive with invention. It’s always been democratic. Fashion Week records it, amplifies it, sometimes even steals from it.
⸻
VREELAND:
Steals? Oh Bill, it dignifies it. It takes the marvelous accident of a girl on Lafayette Street and transforms it into a spectacle at Spring Studios. Without the runway, the marvelous risks becoming invisible — lost in the blur of TikTok.
⸻
HALSTON:
But Diana, spectacle without touch is hollow. The true runway is the body moving freely through the city. If a collection cannot breathe in the subway, it cannot live.
⸻
CUNNINGHAM:
And that’s why I’ll still be outside, photographing. Because out there, you see what survives the day — the wrinkles, the sweat, the subway turnstile. Fashion Week is marvelous theater. But the street is honest.
⸻
DAVID:
You remind me, Bill, that the street has always carried a kind of honesty. But honesty is not always marvelous, Diana would say. So let me ask: when the street dictates the season — when gingham or lace is already a viral staple before it walks a runway — do we lose the avant-garde? Or is this democratization itself the new avant-garde?
⸻
VREELAND:
Democratization, darling, is not avant-garde. It is necessary, yes, delicious even, but the avant-garde must shock, must pull you into a future you did not yet imagine. When I see everyone in gingham, I sigh! The marvelous would be gingham embroidered with LED filaments, or gingham twisted into lace — something no one dared wear until it appeared under the lights.
⸻
HALSTON:
But Diana, the shock today is not spectacle. It is restraint. The true avant-garde is a garment that refuses logos, refuses waste, refuses the easy drama of excess. Imagine a jacket so pure, so functional, it could belong to anyone — and yet drape uniquely on each body. That is the radical gesture now.
⸻
CUNNINGHAM:
I think it’s both. Out there on Seventh Avenue, I see teenagers in thrifted gingham skirts and executives in linen shirts cut with the same ease. That coexistence — high and low, old and new, worn sincerely — that is what feels avant-garde today. It isn’t curated by editors; it’s curated by survival, by joy, by the five dollars you spend in a thrift shop that somehow makes you look like you belong in Vogue.
⸻
VREELAND:
Survival has its own poetry, Bill. But we cannot let fashion shrink into utility. I want people to be seen, to be unforgettable. If the street leads, the runway must still electrify. Otherwise we might as well call it Gingham Week and be done with it.
⸻
HALSTON:
And maybe that’s the question: who is Fashion Week for? For the woman on the subway? For the editors in the front row? Or for the city itself, which will absorb and reinterpret everything it sees?
⸻
CUNNINGHAM:
For the city, always. Because the city wears it first, and the city wears it last.
⸻
DAVID:
Then perhaps New York itself is the designer here — stitching spectacle and survival together with each crossing light.
Theme 2: Technology, Couture, and the Body
DAVID:
This season, as models prepare to walk for Off-White and Toteme, the conversation is not only about fabric, but about filters. AR try-ons, AI models, digital runways — all of it now threads through Fashion Week. Clothes no longer touch only the skin; they touch the algorithm, the avatar, the feed. I wonder, then: what becomes of fashion when half of it is already virtual?
⸻
VREELAND:
Darling, I said it long ago: exaggerate, don’t decorate! And what is the algorithm if not exaggeration made mechanical? I adore that Off-White is leaning into the digital spectacle — clothes as memes, couture as viral image. But never forget: a filter cannot replace the marvelous. It can only magnify it.
⸻
HALSTON:
Digital tools are useful, yes. A Toteme silhouette might appear sharper in AR, easier to imagine in your own wardrobe. But silk still needs to graze the body, cashmere must still be touched. Without that intimacy, the garment becomes content, not clothing. And believe me, content doesn’t drape well.
⸻
CUNNINGHAM:
I see it differently. The sidewalk has always been an archive, and now Instagram grids or TikTok feeds are just more sidewalks. When I scroll after a show, I see the same thing I’d see on 57th Street: people interpreting, remixing, making it their own. The digital is simply another lens. What matters is whether the person behind it is authentic.
⸻
VREELAND:
Authenticity, Bill, is a bore! Give me fantasy! Give me gowns so extravagant they crash the server! If Kors sends a dress down the runway and it trends before the applause dies, then the digital salon has done its job.
⸻
HALSTON:
But fantasy without grounding becomes noise. When everyone can conjure sequins in a filter, what matters is restraint. A garment that resists the temptation of excess will outlast the algorithm’s cycle.
⸻
DAVID:
Then let me press you all further. We’ve seen AI-generated models appear in major magazines. We’ve watched AR filters let shoppers toggle gender, size, even fantasy skins. Tell me: is this digital couture a liberation of the body — or its erasure?
⸻
VREELAND:
Liberation, of course! If a boy in Queens can try on a gown in an instant and see himself as marvelous, that is democracy. That is fantasy made flesh.
⸻
HALSTON:
Erasure, if we forget the body itself. Breath, weight, sweat — these matter. I design for a body in motion, not a body in code.
⸻
CUNNINGHAM:
And yet, I’ve photographed people whose entire look came from a thrift store, then watched their image live forever online. Both are real. The digital doesn’t erase the body; it extends it. But I’ll always look for the moment when life interrupts — a wrinkle, a wind gust, a laugh. That’s where the truth still lives.
⸻
DAVID:
Perhaps it is both: liberation and erasure, promise and peril. A shimmering gown seen in pixels, and then caught in a gust on the West Side Highway.
Theme 3: Sustainability vs. Spectacle
DAVID:
This week, as the lights rise on collections from Kors to SC103, another light shadows the runways: the question of sustainability. New York’s proposed Fashion Act would demand real accountability from the industry. Activists still stage disruptions — PETA, Extinction Rebellion — reminding us that spectacle often carries a cost. And yet, Fashion Week thrives on theater. So I ask: can glamour and survival coexist on the same runway?
⸻
VREELAND:
Darling, of course they can! Glamour without conscience is vulgar, but conscience without glamour is despair. A dress can shimmer responsibly. Think of Diotima’s crochet, hand-made, rooted in tradition yet dazzling under lights. That is the marvelous re-educated.
⸻
HALSTON:
I admire that, Diana, but I would go further. Sustainability is not a costume; it is a principle of design. SC103 showing here for the first time — they build from upcycled materials, cutting with precision, crafting garments meant to last. That is not an accessory to spectacle; it is its replacement. The true luxury now is longevity. Fast fashion is like fast food — cheap, addictive, and it doesn’t age well.
⸻
CUNNINGHAM:
I see it on the street already. People buy less but wear with more imagination. A thrifted blazer, a skirt mended three times, worn with pride. That’s not poverty, it’s poetry. It’s how survival itself becomes style.
⸻
VREELAND:
But Bill, let us not confuse survival with aspiration. A mended skirt is admirable, yes — but without the fantasy of a gown at Kors, where would hope be? People need to dream.
⸻
HALSTON:
Dreams must be breathable, Diana. A gown that dazzles but chokes the planet is not a dream, it is a nightmare.
⸻
CUNNINGHAM:
And perhaps the street decides the balance. If the marvelous is too costly, people will turn away. They already have — choosing resale, choosing vintage, choosing to walk with their own flair rather than chase the new.
⸻
DAVID:
So let me ask plainly: is sustainability a design problem, to be solved by the cut and cloth of the garment — or is it a cultural imagination problem, to be solved by how we define glamour itself?
⸻
VREELAND:
Both! Designers must design responsibly, yes, but the culture must still allow exaggeration. Without it, we are left with beige conscience, and darling, nothing is drearier.
⸻
HALSTON:
Re-imagining glamour itself — that is the task. A gown can whisper instead of shout and still transform a room. Sustainability requires we find beauty in simplicity.
⸻
CUNNINGHAM:
And culture follows what people wear day to day. If resale is the new luxury, then imagination will bend that way too. Glamour will survive, but it will be stitched differently.
⸻
DAVID:
Stitched differently — perhaps that is the definition of this season. Threads of conscience, cut against the grain of spectacle.
Theme 4: Diversity and the New Avant-Garde
DAVID:
This season feels like a hinge in time. On the schedule, names like Michael Kors, Off-White, and Toteme return with confidence. But just as striking are the new voices: Diotima, rooted in Caribbean handcraft; L’Enchanteur, weaving myth and spirituality into fashion; SC103, born from New York’s own experimental downtown. These debuts suggest that diversity itself — in culture, identity, method — has become the avant-garde.
So I ask you: is inclusivity today’s true radicalism? Or has it become a performance, folded into the very spectacle it once opposed?
⸻
VREELAND:
Inclusivity, darling, is marvelous — but only if it astonishes. Diotima’s crochet gowns, made with care and history, are marvelous because they transform labor into fantasy. But when brands simply cast a wider array of faces and call it revolution, I yawn. Inclusivity without imagination is like champagne without bubbles — flat and terribly sad. The avant-garde must still shock.
⸻
HALSTON:
To me, the shock lies in fluidity. SC103’s genderless silhouettes are not mere inclusivity — they are freedom cut into form. A jacket without gender, a dress without prescription. That is the future. Diversity becomes radical when it liberates the body, not when it checks a box.
⸻
CUNNINGHAM:
I see it on the street long before it reaches the runway. Young people mixing masculine and feminine thrift finds, styling themselves into something entirely new. It isn’t curated. It isn’t a campaign. It’s lived. What excites me about these new designers is that they’re listening to that street and bringing it into the tent.
⸻
VREELAND:
But Bill, don’t you see? Without the tent, the street risks being ignored. Fashion Week gives those marvelous sidewalk inventions a megaphone. Imagine L’Enchanteur, with its mythologies and symbols, dazzling under the lights — it transforms private identity into public theater.
⸻
HALSTON:
And yet, Diana, the danger is precisely that theater swallows truth. Fluidity and diversity must remain lived, not staged. Otherwise, we end with diversity as costume — and the costume, as you know, can strangle.
⸻
CUNNINGHAM:
But isn’t there power in seeing someone like yourself reflected on the runway, even if imperfectly? A young designer from Brooklyn, a Caribbean heritage collection, a nonbinary silhouette — it signals that the tent is opening wider.
⸻
DAVID:
Then let me ask you: is the new avant-garde measured by who is on the runway — or by who sits in the front row, who decides, who buys, who is seen?
⸻
VREELAND:
It is always measured by who dares to exaggerate. A front row can be dull, but a gown that rewrites the rules — that is unforgettable.
⸻
HALSTON:
No, it is measured by who feels free to wear it when the lights dim. If a garment liberates someone on the street, then it has succeeded.
⸻
CUNNINGHAM:
I’ll say both. The show and the street are mirrors now. But I’ll keep my lens on the sidewalks. That’s where I find the true avant-garde — unstyled, unplanned, unannounced.
⸻
DAVID:
Perhaps the avant-garde is not in a single garment or a single seat, but in the space between — where identity meets imagination.
Theme 5: The Future of NYFW
DAVID:
Here we are in September 2025. The schedule is set: Michael Kors will open the week, Off-White and Toteme return to the stage, and Diotima, SC103, L’Enchanteur step into the tent for the first time. Outside, TikTok Shop and livestream commerce blur the line between runway and marketplace. Inside, editors, influencers, and buyers still wrestle for seats that are fewer than years past.
So I ask you: what should Fashion Week become, if it is to remain essential? Does it still belong to designers, to the city, or to the people?
⸻
VREELAND:
It belongs to the marvelous, David. Kors must dazzle, Off-White must provoke, SC103 must shock us into a new vision. Whether in a gilded salon or a livestream scroll, the role of Fashion Week is to remind us that life can be larger. It is civic theater — a duty to exaggerate.
⸻
HALSTON:
And yet spectacle alone cannot carry it. Fashion Week must become slower, more intentional. Imagine fewer shows, but garments designed to endure beyond a season. Imagine Off-White not as a flash in the feed, but as a silhouette you could wear for years. If Fashion Week wants a future, it must design for longevity, not applause.
⸻
CUNNINGHAM:
But the truth is, people already look past the runway. On TikTok, a fifteen-second clip of a Kors gown will circulate faster than the reviews. The sidewalk and the scroll are the new front row. If Fashion Week wants to matter, it must serve the people who carry those looks into the city after the photographers have gone.
⸻
VREELAND:
Bill, you are right that the scroll is fast — but it is also forgettable. Fashion Week must still provide the unforgettable moment. A gown that trends, yes, but also a gown that etches itself into memory.
⸻
HALSTON:
But what if the unforgettable moment is a whisper, not a shout? SC103’s upcycled cuts, Diotima’s crochet — they may not set TikTok ablaze, but they breathe with integrity. That may be the only future Fashion Week has: a balance of restraint and spectacle.
⸻
CUNNINGHAM:
I’ll tell you the future as I see it. Fashion Week will survive if it stays porous. The runway feeds the street, the street feeds the feed, the feed feeds back into the runway. If the circle breaks — if the show isolates itself — then it becomes irrelevant.
⸻
DAVID:
Then let me end with this. Should Fashion Week remain what it is — a six-day burst of theater — or dissolve into the everyday spectacle of the city, where every sidewalk, every scroll, every subway ride is its own catwalk?
⸻
VREELAND:
No — it must remain! We need the blaze, the drama, the moment when the city stops to gasp. Without it, the marvelous disappears into banality.
⸻
HALSTON:
Perhaps it should evolve — fewer shows, deeper shows. Still a stage, but one that honors substance over noise.
⸻
CUNNINGHAM:
I think it already has dissolved, David. Look outside: gingham shorts, lace skirts, thrifters with more imagination than budgets. Fashion Week is happening whether the tent rises or not.
⸻
DAVID:
Then perhaps the future of New York Fashion Week is not an answer, but a tension — between blaze and whisper, between runway and sidewalk, between spectacle and survival. And perhaps it is that tension itself that keeps it alive.
Conclusion
DAVID:
Tonight we’ve traveled the avenues and ateliers of fashion’s imagination — from the sidewalk’s honesty to the runway’s spectacle, from the touch of fabric to the shimmer of a filter, from sustainability’s conscience to diversity’s new forms of shock, and finally into the uncertain horizon of Fashion Week itself.
Diana reminded us that exaggeration is a civic duty — that without drama, the marvelous dissolves into banality. Halston offered another truth: that the future may whisper rather than roar, that simplicity and longevity are themselves acts of liberation. And Bill brought us back, again and again, to the sidewalk — to the lived poetry of what people actually wear, and the democracy of style in motion.
As New York Fashion Week unveils the Spring/Summer 2026 collections, these voices remind us that the city itself is the designer — stitching together fantasy and survival, spectacle and restraint, heritage and experiment. Perhaps the real runway is everywhere: in the subway car, in a thrifted gingham skirt, in a gown that trends before the applause fades.
What endures is not just what we wear, but what we dare to imagine through what we wear. That, maybe, is fashion’s true task: to keep inventing new ways of being seen, and new ways of seeing one another.
Thank you for listening. Until next time — keep the conversation alive.