WHAT MEN’S MILAN FASHION WEEK SS27 TAUGHT US

Fun fact: this roundup is being written live from Italy — not at some dramatic expense to feel inspired — but I just so happen to be on holiday. Between Rome, Florence, Milan and Como, it is hard not to fall for the rhythm of this place.

This Milan Fashion Week felt like the most international in a while, marked by the long-awaited return of two major American houses folding into a city renowned for its craftsmanship and artisans. You can see why these names want to be here. Admittedly, it is not easy condensing so many shows into these short snapshots, but for the sake of your time, here is a rundown of my standouts and some lessons I have become the wiser from.

SIMONE ROCHA - MASCULINITY CAN BE GENTLE

Yes, she may have shown at Pitti Uomo — technically not Milan — but this show simply has to be discussed. Irish designer Simone Rocha presented her first standalone men’s show at the Teatro della Pergola in Florence, resulting in what was a deeply romantic study of masculinity. Each look felt like distinct characters: tradesmen, dancers, painters, socialites and more. They moved through a softened, almost theatrical world where identity was fluid. To me, the Simone Rocha man is tender and sensitive, yet confident in knowing exactly who he is.

Rocha’s menswear was interestingly disjointed. Skipper polos and rugby shirts, now house signatures, were reworked in airy taffeta. Tailoring flowed into flou: billowing bermuda shorts that flirted with kilt-like volume, Edwardian jackets, wool overcoats and lamb leather trenches all softened by movement rather than structure. Nylon anoraks were adorned with pie-crust frills and dramatic ruffling, pushing technical fabrics into something romantic, while wagging ivory tulle boas slung over shoulders lifted the darker tones. Floral appliqués throughout, weighty Gladstone bags and professorial layers of knits, shirts and floral ties grounded the collection in a distinct Irish romance, as if these men were poets on their way somewhere with something to do. The apron continues its takeover after Miu Miu SS26, with Rocha adding her own romantic spin on leather and pinafore versions. Imagine that: the fantasy of a man who is domestically in touch. In the day and age of loafers upon loafers, ballet flats signalled the next step in this boyish softening, reimagining delicacy as a new kind of strength. The Simone Rocha man is clearer than ever. He is in touch with his softness. He is pretty yet still a man. He is a doer and more importantly, offers a window into an idealised world where we all take our part.

RALPH LAUREN - MAKE CLASSICS YOUR OWN

After a 20-year hiatus from Milan, senior creative director John Wrazej opened Dream Racers with Purple Label’s quintessential pinstripe tailoring before gradually loosening the dress code into something altogether more spirited. Inspired by what Lauren describes as the “ease and traditions of collegiate style and the gentleman athlete,” each look emerged as though from the dandiest Ivy League soirée imaginable, the models carrying themselves with the buoyant pep of young gentlemen in the making. Sharp tailoring met with rustic boro-patchwork jackets and coats created with Tokyo label Kuon — for if denim is anything, it is American, it is Japanese and it is Ralph Lauren.

The undoubted star of the show was the styling. Espadrilles and loafers lent an effortless ease to the otherwise sophisticated affair. Leather field jackets, cricket jumpers and Breton-striped knits infused the collection with a Mediterranean mood that works hand-in-hand with the brand’s unmistakably preppy attitude. Waistcoats layered beneath moto bombers, a raffia field jacket, denim smoking jackets and boldly patterned formalwear proved that even after 59 years, Ralph Lauren still knows how to make formality feel cool. Polo Ralph Lauren closed in a riot of madras, signature varsity jackets, rugby shirts and brilliant colour, reaffirming the house’s gift for making eclecticism feel timeless. Wrazej embraces Americana maximalism at its most confident and its most unbothered. Above all, the collection celebrated the man who dresses for the joy of dressing, a reminder that great style is as much about confidence and character as it is about the clothes themselves.

THOM BROWNE - HAVE FUN WITH YOUR TAILORING

Where Ralph Lauren excelled in imagination, Thom Browne ventured into outright reverie, standing as one of the few menswear designers that can balance theatricality with sartorial precision so convincingly. Returning to Milan after 18 years, Browne’s fairytale buzzed across his tailoring. Bees, dragonflies, ants and grasshoppers fluttered as embroidery, drawn from childhood classics A Bug’s Life and The Princess and the Frog. The sharpness of the tailoring was softened with hazy pastels, all the more punctuated by flashes of grass green, blood orange and sunshine yellow on parkas, trenches and knits.

Browne's mastery of tailoring remains apparent, never lost in the whimsy. Seersucker fabrics, mesh cardigans and Browne’s unmistakable schoolboy shorts gave the collection a distinct summery ease. Clashing prints and skewed proportions (very Harry Lambert-esque) made the collection feel playful and inventive, with a paint-splattered herringbone jacket standing out as one of its most memorable twists. Naturally, every fairytale deserves a wedding. Browne closed with a white shorts suit engulfed by a plume of tulle, delivering a bridal finale as unabashedly whimsical as the collection itself.

PRADA - JUSTIFY YOURSELF

Who knew that Raf Simons would be the one to bring skinny back? This season at Prada, there was the distinct sense that he had taken the wheel. Alongside Miuccia Prada, the pair introduced Clarity, a collection built around “the notion of choice, of conscious decision.” The collection notes continue: “Rather than reduction, the focus is a distillation, to the fundamental, intentional and meaningful.” The philosophy of rejecting useless design manifested in an “exact, highly controlled silhouette,” with razor-slim jeans dominating look after look, paired with long-sleeve T-shirts and cropped denim jackets in jolts of primary yellow, deep wine and angelic white. Peter Pan-collared leather biker jackets reduced any faffy details to a minimum: utility became the detail. For seasons, the wider, relaxed fit has reigned supreme, yet now the pendulum seems to have swung sharply back.

Precision extended to every detail. Bags clipped directly onto belt loops became part of the silhouette, belts oscillated between oversized statements and thin straps, while ultra-monkstrap shoes foregrounded the collection’s insistence on purposeful design. Geometric knitwear, with wide collars and diaphragm-clinging proportions revealing flashes of shirting beneath, injected personality into an otherwise disciplined wardrobe, while soft-shouldered tailoring in muted greys and black provided some relief. In hindsight, the now much-discussed asymmetrical sunglasses feel less like a gimmick than an invitation to reconsider “ceaseless possibility and reinterpretation.” The duo could not have summarised the collection better, with the garments “striking in their pragmatic simplicity” and “freed from extraneous detail and exaggeration.” But in a week that has demonstrated such incredible styling, why? Prada’s discipline meets Simons’ restless something-to-say instinct to prove that “An exercise in clarity, refusal can be a positive act, an antidote to complication and a means of definition.”

PAUL SMITH - STICK TO YOUR GUNS

The undisputed king of making — and wearing — the British suit, Sir Paul Smith presented a collection that “charted a course through his own history of travel,” drawing inspiration from vintage textiles and marketplace finds from his many excursions. The result felt utterly relaxed. Softened 1950s tailoring, fully unbuttoned shirts, undone ties, open waistcoats and generously cut pleated shorts transformed the suit from something formal into something effortless. If anyone had dared to wear a suit through London’s heat last week, this is probably what they would have looked like (or at least hoped to).

Inspired by street photography of Cairo, airy fabrics in greys and taupes, cut through with moss greens, navy blues and expressive florals, gave the muted palette a personality. Yet its character was found in the styling. Knitted vests, patterned neckwear and the minor details — shirt cuffs folded over jacket sleeves, loose pocket squares and fishing-hook brooches — made each look feel personal with a storied charm. At 79, each of Smith’s collections feels like a step forward from the last. In a time obsessed with chasing the next new thing, he remains one of the few designers confident enough to keep refining what he already knows works.

GIORGIO ARMANI - ELEGANCE CAN BE FOUND IN RESTRAINT

Always the rightful closing act of the week, Giorgio Armani’s show gave a finale of a whopping 160 looks. Presented by menswear creative director Leo Dell’Orco and Silvana Armani, Mediterranean Market blended menswear with a cruise collection inspired by “an open universe shaped by stories, cultures and inspirations that intertwine through travel.” Every look felt like another local wandering through a sun-drenched town square in Capri. Even after he left us last year, his power of consistency endures as a brand value. His unwavering vision, even now, made this one of the lightest, most effortless line-ups of the season.

Faded greens reminiscent of Tuscan fields, the stony neutrals of Grecian coastlines and midnight blues echoed a journey across the Mediterranean, while breezy linens, Cuban shirts and washed button-ups looked as though they had already lived through many summers. These shirts, whether in slubby linen, denim or sheer organza, placed emphasis on the fact they are not clothes necessarily to be admired as much as to be worn. Utilitarian field jackets, pocket-laden bombers and vests gradually gave way to relaxed, fluid tailoring. Soft-shouldered, often collarless cardigan suits in textural fabrics were styled with silk blouses, and shapeless black-tie looks felt worlds away from today’s dress codes. Like Paul Smith beforehand, Armani made the case for the lapel brooch as the season’s accessory of choice. Above all, Armani’s greatest lesson remained the simplest one of all: elegance can be achieved the moment you stop trying too hard.

Let’s talk again soon… about Paris.