Milan Menswear Week Fall/Winter 2026/2027 – Key Shows and Style Trends
Could the Title of Dolce & Gabbana’s Show, ‘Portrait of a Man’, Serve to Caption All of Milan Menswear Week? From Sporty Athlete to Dreamy Romantic, Bohemian Hipster to Bookish Preppy – there’s Without Doubt a Look for Every Man! Question is, What’s Yours?
MILAN MENSWEAR WEEK FALL/WINTER 2026/2027:
DOLCE & GABBANA, PAUL SMITH, PRADA, GIORGIO ARMANI and DSQUARED2
At Dolce & Gabbana
Image Credit Milan Menswear Week, Camera Nazionale della Moda Italiane , WWD and Vogue
Italian men take their fashion very seriously. The famous concept ‘La bella Figura’ (that looking good and feeling good about yourself goes hand in hand with the essence of what it means to be Italian) is very much alive and well in Italy!
Hence, as the iconic Pitti Uomo trade show kicked off another season of finest fashion in Florence – as a precursor to the much anticipated Milan Menswear Fashion Week, the Italian fashion capitol was jam packed with style icons, celebrities and fashionistas soaking up the drama and sex-appeal first hand, front-row and on the streets of Milan.
And indeed the Fall/Winter 2026/7 shows delivered that magical potion of unbeatable Italian flair, testosterone and dramatics.
But let’s not forget it’s the extraordinary creations from the stables of visionaries Giorgio Armani (this will be the first show since the passing of the legend), Paul Smith, Dolce & Gabbana, Tod’s, Etro, Ferragamo, Prada and friends, that we’re really here for …
We’ve made a modest compilation of our favourite shows of the week. Sit back and enjoy the inspiration, the style and glorious innovation (and feel free to draw up that little wish-list of pieces for Fall/Winter 2026/7)!
PRADA
A white shirt was speckled with marks – coffee, cake, cigarettes? It certainly looked like it had been lived in, and had had many life experiences!
Watch Prada’s show here: https://www.youtube.com/watch?v=J1GCDcbYIRI
Slimline, elongated and body-conscious silhouettes defined a collection of pieces by Miuccia Prada and co-designer Raf Simons that is, for those of us who closely follow the evolution of design at Prada, quite telling. It speaks of further refinement, further stripping of all that is unnecessary – a silhouette that is precise and deliberate.
Overcoats and jackets were narrow in cut, sometimes single-breasted, sometimes double-breasted, never voluminous. Trousers, too, were slimline, and slightly elongated at the heel to casually fold at the ankle, exposing bold footwear with sporty bright laces.
Short military-style capelets – some with their hats pressed against the models’ right back shoulder like a compressed flower, came in unexpected pops of colour like boldest turquoise and magenta. These colours were echoed in the distinctive sailor-like hats and hats with their elongated brims protecting the neck from the elements.
Cuffs – plain and striped – were another distinctive feature of this collection. These were oversized and peeked out visibly from underneath knitwear, jackets and coats. Sweaters were delightfully bright – sunshine yellow and tomato red – and came in exaggeratedly low round necks while vests came in an unorthodox T-shape.
Raincoats, overcoats and trench coats (often belted) were softly shaded in mushroom, aubergine and pink, and often looked noticeably crumpled, as if they were hurriedly unpacked for use, without the time or desire to press prior to use. Similarly, a white shirt was speckled with marks – coffee, cake, cigarettes? It certainly looked like it had been lived in, and had had many life experiences!
One can’t help but muse, is Miuccia Prada telling us it’s okay not to fuss over these imperfections, that perhaps there are more important things to fret about in the crazy world we’re living in? That wearing a well-loved piece – albeit not pristine anymore – is totally acceptable, and in fact covetable?
Yet again, from the stables of two intellectual designers came a collection that’s as delightful as it is thought-provoking: always capturing the zeitgeist, never superfluous or wasteful in cloth or ethos.
At Prada
Image Credit WWD
Backstage at Prada
Image Credit WWD
Backstage at Prada
Image Credit WWD
Backstage at Prada
Image Credit WWD
Backstage at Prada
At Prada
At Prada
At Prada
At Prada
At Prada
At Prada
DOLCE & GABBANA
Whether you’re a bohemian 60s hippie or a corporate statistician, a romantic idealist or pragmatist, Dolce & Gabbana has you covered!
Watch Dolce & Gabbana’s Show here: https://www.youtube.com/watch?v=iz6jJLeYJaI
‘Portrait of a Man’ – the title of Dolce & Gabbana’s show – could easily have been been captioned ‘Portrait of Many Men’, as the array of potential looks most certainly extends well beyond even the most eclectic of dressers! However, we assume the intention was to illustrate the multiplicity of looks that a man may wish to embody.
There’s a potential look for just about every man within the offering – from the athletic, sexy beast to the preppy, bookish guy who loves his soft tailoring. Whether you’re a bohemian 60s hippie or a corporate statistician, a romantic idealist or pragmatist, Dolce & Gabbana has you covered! That being said, the banner that unites the multitude of Dolce & Gabbana men, though, is as ever, the tried-and-tested Dolce & Gabbana recipe: more than a pinch of sex-appeal.
Opulent faux fur coats shouted, unwrap me! Ripped jeans, black leather and leopard print details oozed with glamour and sensuality. Pyjama suits suggested relaxation and perhaps more… and pinstripes spoke a language of understated sexiness, whereas pirate coats, cleavage and lace-up knee-high boats evoked an escapist narrative of being hijacked on the high seas.
Even ‘gangster’ suits with their wide lapels and dark sunglasses made an appearance. Velvet jackets, hussar coats, leopard print housecoats, smoking jackets and shearling overcoats all expressed a decadent luxe and opulence. Jewellery featured strongly – heirloom watches on long gold chains decorated oversized lapels.
It’s evident there was absolutely nothing apologetic or subtle about this collection. It was all about being super bold, bright and uber-confident – whichever sphere or stage of life you find yourself in. Think ‘male birds of the animal kingdom’ – not the demure female ones – and you’ll be spot on.
At Dolce & Gabban
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabban
At Dolce & Gabbana
At Dolce & Gabbana
At Dolce & Gabbana
GIORGIO ARMANI
Quirky novel details inspired by a fresh eye, appeared in Dell’Orco’s offering: somehow colours were a tad more adventurous, tailoring a little sharper – and one may say the whole look was somewhat ‘updated’.
Watch Giorgio Armani’s Show here: https://www.youtube.com/watch?v=j4qA9u9sjqs
Many in the world of fashion understandably held their breath since Armani passed away in September 2025 – who could possibly replace the inimitable, long-reigning high priest of Italian fashion?
A Fall/Winter 2026/7 show entitled ‘Cangiante’ (‘iridescent’) was the brainchild of the late Armani’s disciple and his partner of forty years, Leo Dell’Orco.
Dell’Orco utilized a deliciously tactile array of fabrics – some silky and iridescent, but also velvet, cashmere, matt leather, felted wool, chenille and tweed – to showcase the first menswear collection without the direct input of Giorgio Armani.
The collection was indisputably ‘Armani’ – from the signature soft tailoring around the shoulders, the Nehru collars, trench coats, tweed boucle, bomber jackets and pristine white shirts to the luxe volume of the immaculate, pleated trousers and (mostly) neutral colour palette.
However, quirky and fabulous novel details inspired by a fresh eye also appeared in the inevitably ‘new’ mix: somehow colours were just a tad more adventurous (jewel tones like lapis, purple, acqua, teal and loden), the tailoring just a little sharper – and one may say (no disrespect to Mr Armani), the whole caboodle somewhat ‘updated’.
But perhaps the most striking memory of the ‘new’ Giorgio Armani show was Leo Dell’Orco appearing in a double-breasted tailored suit at the end of the show – as opposed to the image we all have in our mind’s eye of the legendary Giorgio Armani in his iconic dark T-shirt.
All in all, we’re quietly confident brand Giorgio Armani will retain its signature features (phew!) but at the same time super excited to look forward to a new chapter of incredible creations in the more than capable hands of Leo Dell’Orco.
Image Credit WWD
Backstage at Giorgio Armani
Image Credit WWD
Backstage at Giorgio Armani
Image Credit WWD
Backstage at Giorgio Armani
Image Credit WWD
Backstage at Giorgio Armani
Image Credit WWD
Backstage at Giorgio Armani
At Gorgio Armani
At Gorgio Armani
At Gorgio Armani
At Gorgio Armani
At Gorgio Armani
At Gorgio Armani
PAUL SMITH
The signature easy, slouchy Brit-style tailoring came through strongly.
At almost 80 years old, veteran designer Paul Smith certainly earns the right to admit he’s looked over his archival collections (especially those from the 1980s) to conjure up what was a masterful offering for Fall/Winter 2026/7. Homage was paid in this collection to Yves Saint Laurent and Chanel shows the designer fondly remembers having seen as a young person.
The signature easy, slouchy Brit-style tailoring came through strongly, often constructed in traditional Donegal and herringbone tweeds. Endearing Fair Isle hand-knits, flatcaps, car coats and classical white shirts all painted a picture of a British country estate leisure.
Anoraks and macs completed the picture of Brit-cool. Bold prints (a Paul Smith fingerprint) and bright colours added to the collection that no doubt thrilled every Paul Smith enthusiast.
Soft grey and charcoal sat nicely beside sand, mustard and biscuit shades, with the occasional bolt of sky blue or lemon yellow popping for effect.
An appliqued jacket stood out as one of the most memorable pieces in a collection that is soothing and soft, reassuring and effortless.
At Paul Smith
At Paul Smit
At Paul Smith
At Paul Smit
At Paul Smit
DSQUARED2
Ready for the Olympics, anyone?
Watch Dsquared2’s Show here: https://www.youtube.com/watch?v=Y14HpODjHcY
There was a decidedly Winter Olympics feel to the offering by twins Dean and Dan Caten’s brand Dsquared2’in Milan – even the runway was a fake snow-covered stairway.
The scenery may have been frozen, but the fashion – and its uber-seductive bearers – were HOT! Steamy and sensual, models came down the stairway looking as if they’ve stepped straight out of a glamour magazine, oozing sex appeal and effortless chic.
Après-ski ruled the roost, with fur collars, puffer jackets, oversized ski hats, vinyl and snow-resistant leathers looking suave and sporty, but other Olympic sports also featured: hockey, for example (incidentally, Canadian actor Hudson Williams opened the show, who starred in the gay hockey love story ‘Heated Rivalry’), with layered hockey jerseys, skinny jeans and ice skater boots looking very athletic indeed.
Ripped double denim jackets and jeans, padded vests, parkas, chunky knitwear and voluminous coats added to the sporty & sexy ambience, and one could instantly picture the innumerable ways of layering, mixing and matching the various items in this racy collection.
The colours popped unapologetically, all beautifully framed against the pristine white backdrop of fake snow.
Olympic imagery was to be seen in many places, but the gold medal goes to… the extraordinary footwear! Female models presented a hybrid high heel that, as if by magic, conveniently snapped into a practical ski boot.
And the wizardry didn’t stop there: ski goggles would effortlessly morph into sunglasses! And who wouldn’t want to see the world today through all-singing and all-dancing rose-coloured specs?
At Dsquared2
At Dsquared2
At Dsquared2
At Dsquared2
At Dsquared2
At Dsquared2
At Dsquared2
At Dsquared2
For any questions/feedback regarding the above mentioned products/brands, please do contact us anytime by clicking here
