Milan Fashion Week: Skirts, Sabotage, and the State of Italian Luxury

Milan’s shows revealed a fashion industry in transition, with established houses like Gucci, Armani, and Bottega cycling through creative directors while newer talents like Demna and Simone Rocha prove their worth through collections that actually sell.

Summary of Duomo Days. Every timestamp links into the original audio.

The short version

• 00:16:51 — Prada’s focus on a single silhouette—the skirt—set the tone for the week and demonstrated how one strong directional idea can lead the entire fashion conversation.
• 00:17:08 — Milan fashion week functions differently than Paris; the Italian schedule tells a cohesive story about what’s happening in the industry rather than presenting a disparate collection of shows.
• 00:19:41 — Reporting indicated that Miuccia gives Raf Simons the directional vision while he executes the designs, though the exact balance of their collaboration remains unclear even to industry insiders.
• 00:25:11 — Jill Sander showed how contemporary tailoring should work for the next generation—creating office-appropriate silhouettes that feel current and desirable without referencing existing trends.
• 00:31:07 — Marni successfully tapped into thrifting culture and mismatched styling in a way that appeals to people who want contemporary fashion without being actual Gen Z thrifters.
• 00:41:47 — Demna Gvasalia’s first Gucci collection functioned as a holding pattern, establishing bourgeois sensibility while the fashion world waits for him to settle into the role and add his signature cynicism.
• 00:46:15 — Giorgio Armani’s succession plan involves Dario bringing his vision to Emporio first while Silvana continues the main line, with expectations that the transition will accelerate once the company sells to new ownership.
• 00:48:34 — Dolce & Gabbana showed meaningful improvement with a new CEO and direction, moving away from being stuck in the past toward engaging with current fashion conversations while maintaining their core strength in fit.
• 00:54:33 — Bottega Veneta’s fundamental challenge is that Louise Trotter lacks a distinctive creative vision and would benefit from a strong collaborator to elevate the brand beyond its impressive craft and leather goods.

In depth

Why Prada’s skirt became the week’s organizing idea

Lauren Sherman argued that Milan behaves differently from Paris precisely because it is compact enough to read as a single narrative, and that Prada, now shown on Tuesday instead of Thursday, effectively sets the terms for everything that follows 00:17:08. The mechanism she points to is not novelty for its own sake but focus: Prada and Raf Simons built an entire season around one silhouette, the knee-length skirt, and let styling, accessories, and even the choice to bare skin do the work of making a prim shape feel aggressive 00:19:05. Becky Malinsky’s read was that the skirt-as-concept itself felt more like a Raf move than a Miuccia one, guessing that his instinct is to seize a single strong idea and run with it, whereas she pictures Mrs. Prada wanting to dig deeper into the psychology of a garment rather than declare it the whole show 00:18:11.

Both hosts complicate their own read of the partnership. Lauren says her reporting suggests Miuccia sets the direction and Raf executes it, a claim she immediately hedges by noting that no one outside a marriage really knows how creative decisions get made inside one 00:19:41. She also points to color as an area where Raf’s hand feels more visible since he joined, which cuts against a clean division of labor where he’s merely the executor 00:20:48. Malik’s listen-through of the Prada/Simons Vogue podcast added texture but not resolution: the two designers described a compressed development timeline and a collaborative back-and-forth rather than a hierarchy, and the most concrete detail to emerge was biographical (Miuccia’s daily lunch-with-granddaughter routine) rather than a clarification of who owns which ideas 00:22:23.

The unresolved tension is really about bra tops and half-looks. Malinsky is fatigued by exposed midriffs and bloomers across the industry and wants a full outfit as the actual creative challenge, yet she bought the Prada bra top anyway 00:18:41. Sherman’s explanation is functional, not aesthetic: because the message from this design duo has trended tough and severe for several seasons, and a knee skirt reads inherently proper, skin becomes the only available lever left to keep the show feeling transgressive 00:18:50. Neither of them fully resolves whether that’s a smart solution to a styling problem or a symptom of an industry-wide crutch.

Jill Sander as the answer to a market gap

Sherman’s strongest, least qualified praise of the week went to Jill Sander, and she frames it as solving a specific commercial problem: there is almost no brand right now making tailoring that feels current rather than corporate or referential 00:25:19. Her argument is that Theory-style workwear already covers the office, but nothing else on the market offers a woman a way to dress with some polish that isn’t jeans, and that Simone Bellotti’s collection filled that exact gap with slim long jackets, flared trousers with a bit of drape, and fabrics with texture 00:25:33. She goes further, insisting the show didn’t quote any recognizable predecessor or house code — it just looked new, which she treats as a rarer achievement than it sounds 00:26:05.

Malinsky’s addition is a theory about creative freedom: she thinks this was the first season where Bellotti felt able to design without a hundred people telling him what “Jill” is supposed to mean, and that the resulting collection is looser and less disciplined than his earlier work in a way she reads as liberating rather than sloppy 00:26:19. Sherman agrees, calling it less buttoned-up than his prior seasons, and both hosts independently produced almost the same anecdote as evidence: people who saw the showroom afterward, unprompted, told them how good it looked in person, right down to specific reactions to the shoes 00:27:02.

What makes this section more than a rave is the pricing digression, which turns the show into an argument about retail viability. Malinsky flags that European pricing on Jill Sander, boosted by the VAT refund tourists get, makes a blazer meaningfully cheaper to buy in Milan than in the U.S., where she calls the American pricing prohibitive 00:59:55. Sherman narrows her own shortlist of brands she’d actually spend money on to essentially three names — Phoebe Philo, Jill Sander, and Prada — explicitly noting that admiration for a collection and willingness to buy it are two different currencies, and that most of what she wears day to day is vintage rather than current runway product 00:27:43.

Demna at Gucci: read as a transition, not a verdict

Both hosts treat Demna Gvasalia’s Gucci debut less as a finished statement than as a strategic first move, and they disagree with each other about whether that was the right first move. Sherman’s position is that Gucci, post-Alessandro Michele, needed to reset toward something bourgeois and preppy, and that several other designers — she names Jonathan Anderson and Michael Rider — would have made more obvious sense for that particular repositioning 00:40:00. Her read is that Kering didn’t really have the luxury of options at that level of talent, and that Demna both wanted the job and effectively rescued the house by taking it when there was no deep bench of alternatives after Sabato De Sarno’s exit 00:40:18.

Sherman’s other argument is structural: she thinks Demna staged the show explicitly as a design audition, walking through eras of Gucci history back to before it was a designer-driven brand, which she reads as the smart move for a first outing precisely because it survives on craft and product rather than on a directorial vision that hasn’t yet cohered 00:41:00. She backs this with her own wallet, describing a navy skirt from the pre-collection that has no pockets, cost a lot even with a generous discount, and that she still loves wearing 00:41:36.

Where the two push back on each other is over tone. Sherman’s account of the makeup — heavy, goth, applied over what she considered the strongest, most Sloane Ranger-adjacent womenswear looks — is framed as actively working against the clothes, both in person and in photographs, and Malinsky agrees this was a rare point of total consensus between them 00:39:10. More substantively, Sherman argues that whatever Demna does, he does it with an inherent cynicism that has nothing to do with intention — it’s simply his design sensibility — and that this is a mismatch with Gucci’s historical identity, which she calls not a cynical brand 00:42:51. Her conclusion is deliberately unresolved: individual pieces are excellent and the accessories will likely sell regardless of whether the show communicates a coherent emotional message, but whether Demna ever settles into a version of the house that feels less detached is an open question she compares, without fully committing to the parallel, to Hedi Slimane’s rocky first Celine season before his second, more accepted one 00:43:28.

Armani’s accelerating succession and Dolce’s quiet turnaround

The Armani discussion is really about pacing. Both hosts describe Emporio Armani’s collection as essentially a placeholder — competent, wearable, largely white and neutral — while the real story is the handover to Dario, who is doing Emporio now and expected to eventually inherit the main line’s design duties, with Silvana Armani continuing to design Giorgio Armani proper in the interim 00:46:15. Sherman’s contribution is a prediction with a specific mechanism attached: she thinks the timeline will compress dramatically the moment Kering’s stake sale (or whichever ownership change is in motion) closes, rather than unfolding over the previously assumed two-year runway, and she cites Marco Bizzarri’s visible presence at the show, plus his prior relationship with Alessandro Michele, as circumstantial evidence that he had a hand in installing Dario and will push the transition faster 00:47:37. She hedges this only slightly, framing it as informed speculation from industry conversations rather than confirmed reporting.

Her underlying argument about why speed suddenly matters is about audience patience: when Giorgio Armani himself was alive and designing every collection identically season after season, that consistency read as intentional and was accepted as the point of the brand — it was positioned as a style house rather than a fashion house, and the recent Armani campaigns had, in her view, been unusually strong, reinforcing that this was a deliberate identity rather than stagnation 00:47:17. Now that the designer is gone, she thinks audiences will lose tolerance for that sameness much faster, making the case for accelerating Dario’s authority rather than easing into it gradually.

Dolce & Gabbana gets a smaller but pointed treatment as the week’s most surprising improvement. Sherman describes the show as feeling more integrated into the current fashion conversation than Dolce’s recent history of being stylistically frozen in an earlier era, comparing it to a version of the house inflected with more of a Chanel-like polish 00:48:34. She attributes the shift partly to new CEO Stefano Cantino, whose résumé spans Gucci, Bottega Veneta and Prada in communications and image roles, arguing that his experience gives him a strong sense of how to modernize a heritage house without abandoning what already works — namely Dolce’s continued strength in fit and construction, which she says makes the clothes durably desirable to people who dress real people rather than just runway bodies 00:49:45.

Bottega Veneta’s proportions problem and the search for a collaborator

The most pointed critical thread of the episode is aimed at Louise Trotter’s Bottega Veneta, and it’s notable that both hosts frame their criticism as sympathetic rather than dismissive — they explicitly say they want her to succeed and describe her, by reputation, as gracious and easy to work with 00:54:59. The substance of the critique operates on two separate levels that they take care to distinguish. The first is a career-long criticism Sherman raises directly: that Trotter has historically worked from other people’s ideas rather than asserting a fully original point of view, and that at Bottega this has compounded into a brand now defined by craft and leather-goods excellence with no clearly legible authorial voice behind it — she says she can identify Michael Rider’s hand, Phoebe Philo’s hand, but not Trotter’s 00:54:27.

The second, more concrete problem is fit, and here Malinsky does the closer diagnostic work. She notes that the runway silhouettes are oversized to the point of looking unfinished on six-foot models, and argues this isn’t a stylistic choice so much as an execution issue: menswear at the same show fits properly and reads well, while the women’s pieces are cut too wide through the shoulders and body, making them nearly impossible to translate to a woman of average height once they reach retail 00:55:41. She’s careful to separate this from Trotter’s own personal style of wearing oversized clothing well despite being petite, arguing that whatever works on Trotter herself isn’t automatically translating through the design process onto the runway body 00:57:36.

Their proposed fix is a collaborator, not a replacement, with Sherman singling out that Trotter no longer appears to be working closely with stylist Suzanne Koller and suggesting the earlier partnership had become too insular to produce an outside perspective 00:54:48. They note the men’s line and the house’s shoes are strong enough on their own to survive a stronger creative hand, and Malinsky specifically points to Trotter’s past sportswear work at Lacoste and Joseph as evidence she has the raw ability, just not currently the collaborator or discipline to apply it at Bottega’s scale 00:58:19. Underneath all of it sits an admission that Kering as a whole is mid-upheaval, with Sherman speculating that within two years nearly every creative director across the group’s brands could be new, and that, oddly, Trotter — despite this critique — may be the one currently in the most stable position of any of them 00:56:45.

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