How Digital-First Fashion Culture Created the "Simulation Era" and Why Luxury Brands Are Fighting Back

As AI makes perfect digital imagery easier to create, luxury brands are discovering that handmade art and in-person experiences now feel more aspirational than algorithmic perfection.

Summary of Has Fashion Had Enough of AI?. Every timestamp links into the original audio.

The short version

• 00:02:50 — The clothes we see online have become more important than the physical garments themselves, fundamentally changing how fashion is designed and merchandised.
• 00:03:32 — Logos have become increasingly dominant on garments because they are the only details visible in small digital images, reducing incentive to invest in construction quality or fabric texture.
• 00:04:38 — Consumers experience alienation when products arrive looking nothing like their online images, creating a cycle that has contributed to the recent decline in the luxury sector.
• 00:06:12 — Luxury brands have raised prices without increasing quality or creativity to match, frustrating shoppers who question whether expensive items are actually worth buying.
• 00:07:00 — Artificial intelligence could worsen the simulation problem by generating realistic images of products that don’t physically exist, but it could also benefit small designers by automating tedious tasks.
• 00:09:16 — Luxury brands are hiring real artists and illustrators because human-created art now signals genuine luxury more effectively than machine-perfect digital imagery.
• 00:13:30 — Brands are hosting hands-on classes, needle-point workshops, and phone-free dinners that physically prevent attendees from using devices, creating forced moments of human connection.
• 00:17:18 — Instead of measuring success through social media volume and engagement metrics, brands increasingly focus on customer retention and long-term relationship depth with a smaller number of influencers.
• 00:18:55 — The future likely involves coexistence of digital and physical approaches rather than dominance of either, with consumers increasingly questioning which technologies genuinely improve their lives.

In depth

What Rapkin means by the simulation era

Mark Bain’s framing, drawn from his conversation with critic Eugene Rapkin, is that fashion has entered a period where the image of a garment carries more weight in a shopper’s mind than the garment itself 00:02:50. This isn’t presented as a metaphor so much as a description of how design decisions actually get made now: because consumers overwhelmingly encounter clothing first as a photo on a phone screen, brands have reoriented what they produce toward what reads well at that scale 00:03:03.

The clearest symptom, according to Bain, is the swelling prominence of logos 00:03:32. He’s careful to note this isn’t a new phenomenon invented by Instagram, but it has been intensified by it. On a small screen, fabric weight, stitching, and hand-feel are simply illegible, while a logo remains identifiable no matter how compressed or small the image. Once the logo becomes the primary unit of communication, Bain argues, the incentive to invest in the harder-to-photograph aspects of quality — construction, texture, craftsmanship — quietly erodes 00:03:32. The garment is optimized to be recognized, not necessarily to be worn.

Rapkin’s theoretical anchor for the consumer-facing consequence is a concept of alienation borrowed from French theory: when people relate to products mainly through images rather than the physical items, they become disconnected from what they actually own 00:05:04. Bain illustrates this with the meme-ified gap between what’s ordered online and what arrives — a joke usually pinned on Shein, but which he says Rapkin extends to luxury fashion as well 00:05:27. The claim on the table is that this gap isn’t incidental; it’s the structural result of a system where the sale is closed by an image, not an object.

Does digital culture actually explain declining quality — or just enable it?

The most contested moment of the conversation is when Sheena Butler-Young pushes Bain directly: does he actually believe the digital-first mentality is responsible for the well-documented decline in luxury quality relative to price hikes 00:06:12? Bain’s answer is notably hedged. He agrees the online-first mindset is ‘a part’ of the story, but stops well short of calling it the primary cause, and explicitly says he’s not sure it’s even the main driver 00:14:57.

His reasoning is that quality decline has structural causes that predate and run parallel to social media: decades of consolidation and corporatization within fashion houses, and the practical disappearance of certain traditional construction techniques from the supply chain entirely 00:15:09. He offers a personal example — trying and failing to find boots built with a Goodyear welt, an old-fashioned resoleable construction method that has become nearly impossible to source because everything is now cemented or glued instead 00:15:28. His point is that this kind of degradation happens at the level of manufacturing and sourcing, invisible in a photograph either way — nobody assesses a boot’s welt from an Instagram post, so social media can’t be blamed for its disappearance.

At the same time, Bain doesn’t dismiss the digital-image explanation outright. He recounts Rapkin’s own admission of surprise at the resurgence of ‘quiet luxury,’ a trend built entirely around subtle details that don’t translate to images at all — which suggests the image-first economy doesn’t fully explain consumer taste either 00:16:07. Butler-Young pushes further, floating a harsher version of the thesis: that brands may have consciously exploited the fact that shoppers can’t detect shoddy construction online, using digital opacity as cover for cutting corners 00:16:33. Bain doesn’t fully endorse this stronger, more ‘insidious’ reading, but he doesn’t reject it either — he leaves it as a plausible contributing dynamic rather than the central mechanism, which is the closest the episode gets to genuine unresolved disagreement.

AI as accelerant and as escape hatch

When the discussion turns to artificial intelligence, Bain frames Rapkin’s position as essentially agnostic about technology itself: AI is a tool, and its moral valence depends entirely on how it’s deployed 00:07:16. This matters because it lets Bain hold two seemingly opposite claims at once. On one hand, AI plausibly deepens the simulation problem beyond anything photography could do — a photograph is at least a reference to a real object, however flattering, whereas AI-generated imagery can depict a garment that has no physical counterpart at all 00:07:42. That severs the last remaining tether between image and reality that even a heavily edited product photo still preserved.

On the other hand, Bain argues AI could genuinely help smaller players, using his own past experience working for a small fashion label as a reference point 00:07:59. If a small designer can offload tedious administrative work — writing routine purchase-order emails, for instance — to AI, that frees up time and attention for the actually creative parts of the job 00:08:14. Butler-Young presses on this distinction directly, noting that nothing in Bain’s account suggests AI is being used to make the art or the design itself better — only to clear space around it 00:08:32. Bain doesn’t contest this; the improvement AI offers, in his telling, is logistical rather than creative.

Diana Pearl’s reporting on the artist-hiring trend complicates the picture further by suggesting AI’s cultural effect has been almost the opposite of what technologists might have predicted: rather than making synthetic perfection more desirable, it has made flawless digital polish look cheap and suspicious, an association she summarizes as ‘slop’ 00:09:22. That inversion — where the hyper-refined image now reads as inauthentic rather than aspirational — is presented as the direct cause of brands turning back toward hand-drawn, human-made marketing.

The turn to real artists, and how brands can get it wrong

Pearl’s story, reported by colleague Haley Crawford, documents brands like Hermès and Aliéve commissioning painters and illustrators for campaigns, which she reads as a deliberate signal of authenticity rather than a nostalgic gesture 00:08:45. Her argument connects this to a broader cultural mood: the same instinct driving people back toward analog hobbies like needlepoint, knitting, and film cameras is what makes commissioned art newly persuasive as marketing 00:09:44. The implicit brand logic, per Pearl, is that visible human craft in the marketing is meant to imply — even if it doesn’t guarantee — craft in the product itself 00:10:05.

But Pearl is explicit that this move can misfire, and Butler-Young pushes her to specify how. The clearest failure mode she names is opportunism: a brand caught using AI imagery and facing backlash, then pivoting the following week to hire an artist purely as a corrective gesture, without any deeper connection to that artist or to the brand’s own story 00:10:17. Pearl’s standard for doing it well is specificity — she points to Hermès commissioning an artist for store windows in Switzerland who then went on to create ongoing hand-drawn work for the brand’s website, arguing that continuity and prior relationship are what separate genuine craft signaling from a trend hop 00:11:23.

Pearl also raises the more paradoxical risk that this backlash-to-AI can itself become a bandwagon with its own tells — she and Butler-Young note the possibility of brands overcorrecting into visibly imperfect or ‘human’ markers, like a deliberate typo, purely to prove authenticity rather than because it serves the work 00:10:37. Neither speaker resolves how a brand is supposed to tell the difference between authentic craft and staged authenticity from the outside, which leaves the standard Pearl proposes — internal consistency with brand story — as more of a heuristic than a hard test.

Measuring success when you deliberately reduce content

The phone-free dinner and hands-on-workshop trend raises an obvious operational problem that Butler-Young presses Pearl on: if the entire point of these events is to physically prevent guests from generating social content, how does a brand justify the spend without the usual flood of posts and stories to show for it 00:17:03? Pearl’s answer reframes the goal itself — she argues the industry is shifting away from chasing volume and follower count toward prioritizing depth of relationship with a smaller, more selective set of partners 00:17:19.

Concretely, this means Pearl expects brands to move away from classic media-value metrics like earned media value or impressions, and toward slower signals: whether an influencer relationship that began at one of these events persists over time, and whether that longer relationship eventually shows up in sales conversions 00:18:00. She’s candid that this is a harder case to make internally, since depth of relationship is inherently less quantifiable than a follower count or an engagement rate, and she frames it as something brands have to be willing to invest in on faith that it compounds over time 00:18:29.

Both Pearl and Bain end up landing on a similarly cautious, non-triumphant note about where this all goes. Pearl draws an explicit parallel to e-commerce’s premature obituary for physical retail, arguing that the pandemic-era prediction that brick-and-mortar was finished has been reversed by the realization that purely virtual experience can’t build a brand or sustain a life on its own 00:19:35. Bain agrees but resists framing it as physical winning over digital; his closing view is that the two will keep coexisting and adapting to each other in cycles, with backlash following adoption indefinitely, rather than settling into any permanent equilibrium 00:20:29. Neither speaker claims the tension gets resolved — only that it keeps being renegotiated.

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