With the Italian leg of the menswear circuit calling it a day, here’s the Man About Town recap.
In case you weren’t in Milan for Fashion Week, there’s one thing you need to know: it was hot. Not just “I’m not going to bring my jacket for dinner tonight” hot but repeated phone-overheating, handheld fan-carrying hot. Luckily for us, the menswear on show made all the sweating and three-shower days worth it. The tailoring was in abundance, as is typical in Milan, and the collections this season seemed to ease the rigidity of formal menswear for a more relaxed take. So, without further ado, here are our menswear highlights from Milan Fashion Week SS27.
Giorgio Armani soaks in the sun
When it comes to laid-back yet put-together tailoring, not many names come close to the legend that is Giorgio Armani. This season, the late designer’s successors Leo Dell’Orco and Silvana Armani boosted the chill even further, opting for crumpled and sun-bleached iterations of their signature tailoring looks to give a lived-in feel that, rather than looking sloppy, felt more full of character. That same relaxed energy was translated into the suiting itself, making lapels thinner and shorter or getting rid of them altogether for a collarless look that could be buttoned asymmetrically. Even knits looked well-loved, dropping on the body closely like it had been stretched and slightly wet from ocean splashes. The legacy of Armani’s unbeatable casual tailoring lives on!
Brunello Cucinelli wants you to think more
Brunello Cucinelli doesn’t unveil a new collection from nowhere. He introduces it thoughtfully, first over dinner in Florence on the first day of Pitti Uomo, then in the event’s trade fair before a final pitstop in Milan.
Fittingly, the Italian stalwart’s latest offering is centered around the phrase ‘thought is free’. You might recognise those words from William Shakespeare’s The Tempest, spoken by a drunk Stefano, announcing that thought cannot be controlled, which applies to how you contemplate dressing, too.
In the context of Brunello Cucinelli’s latest collection, this means clothing for a free-thinking wearer, unbound by dress codes and conventions who instead applies his own lived experience, knowledge and understanding to his attire. The result? It’s a mix of practical cargo trousers and hardy denim, primed for pairing with indulgent shawl collar tailoring and shirts, T-shirts, or polos in ivory, sand, and tobacco. Materials range from wools to linen and suede. Some looks are finished with a tie, others without. It’s a wardrobe designed to take on the personality of its wearer. All you need to do is think.
Paul Smith takes notes from new-gen suit obsessives
When you’ve been in the game since 1970, like Paul Smith, the archives are a very fruitful source of inspiration.
Today, the brand presented its Spring/Summer 2027 show in Milan with a collection “seen through the eyes of my young staff,” as the namesake designer shared backstage, in front of runway shots from the ’80s and ’90s referencing his colleagues’ delight upon visits to the archives.
That meant a roster of massive suits, both single-breasted (some with a more traditional three-button closure) and double, along with loose shirts in light airy cottons, silk, and linen all worn unfastened, which felt fitting given the scorching heat outside. Trousers pooled over loafers and some ditched traditional waistbands to fold over the belt, while shorts were shrunken and tailored.
What does this say about menswear now? We’re still digging the past. Swishy power suits are holding strong. And dressing down the classics still slaps.
Setchu is a big catch
After an epiphany in Gabon that involved the resilient fishing nets used there locally, Setchu’s Satoshi Kuwata took this on as the foundational inspiration for his Spring/Summer 2026 collection.
Spanning a concise 17 looks, fishing nets were quite literally thrown onto ocean blue, pinstriped tailoring and woven hats, mimicking a veil for the headpiece. A top also features metallic hoops that are woven and constructed with gauze that creates holes, as if a knit has been picked at and nibbled by fish. Kuwata’s Japanese background also came through in the form of a tatami biker jacket that’s so stiff that it features detachable sleeves for a little bit more practicality.
The scenes were at Shinyakozuka
Courtesy of Shinyakozuka
Following a very snowy showing last season for his debut at Pitti Uomo, the winter weather has cleared up for the Japan-hailing Shinyakozuka as the scenery takes a turn for the better.
Kozuka-isms are ever-present through the ultra-wide leg and pleated bottoms that show off his admiration for exaggerated cuts. He swaps out the colder landscapes for summer-ready backdrops like water-coloured strokes of sky blues, rusty oranges and pond-like teals. Flow seemed to be the common denominator, with shirts draping relaxed and oversized – and the same can be said for an almost ankle-grazing t-shirt that’s worn as a dress. Workwear codes still play a part in the form of sets that see chore jackets and blouson-style work jackets paired with matching, cropped bottoms cut with a perfect shorter break.
Summer’s the best time to enjoy nature’s most beautiful scenery. But if you’re in SS27 Shinyakozuka, you can also be the view.
Church’s dug deep into the archives
When you’ve been making shoes since 1873, like Church’s, your archives are stacked. And for the English shoemaker’s Spring/Summer 2027 presentation, it took over the Fondazione Adolfo Pini in Milan, a space that has never been used for a fashion show or presentation before. Inside, some of its oldest models, spanning back to the 19th century, were dotted amongst the artworks on the walls alongside archive ads and new shoes for the season ahead. A pair of collapsible suede slippers are a standout offering, which in 40 degree heat is primed for padding from a Milanese Palazzo to a Negroni-heavy dinner.
Montblanc’s leather goods are the main character in Milan
Travel is a huge part of what Montblanc does. And for Spring/Summer 2027, the brand placed its Writing Traveller briefcase under the spotlight with a roster of new colours and the help of a not-so-subtle supersized version at the heart of the brand’s Milan presentation. Inside, you can hold your pens (this is a Maison that has placed writing at its core since being founded in 1906), as well as your watch, with plenty of room for anything else you might need on the road. It also unveiled the design in softer leathers, known as the ‘Soft Traveller’, offering a less rigid style if that’s your thing. But no matter where you land, rest-assured you’ll arrive at your destination looking like someone with their life together.
Thom Browne’s bugs, beekeepers, and brides take Milan
Before this season, Thom Browne hadn’t shown a collection in Milan since 2008. Naturally its return to Italy’s style capital came with its own boatload of hype, with Jamie Campbell Bower, Curry Barker, and Tramell Tillman all pulling up for their twisted preppy menswear hit. Inside the show venue, models snaked their way around 400 fabric plant pots, first with a trio of seersucker-suited dudes with beekeeping veils draped from their boater hats, then a gaggle of cropped tailoring-wearing lads followed, before an army of plaid jackets arrived. Pops of vibrant reds and greens and blues were dropped into the mix via bags and trench coats. The ender, though? That came in the form of a suit-meets-bridal gown swishing down the runway. Quite the comeback, hey?
Brioni can also kick its feet up
Known as the first menswear label to ever put on a fashion show back in 1952, Brioni’s skin in the game is no joke. They’ve since become the gold standard for high-life, fine tailoring for countless icons and legends throughout the years, including Leonardo DiCaprio, Matthew McConaughey and Glen Powell.
For the SS27 season, the Italian suitmakers took to their hometown of Rome for inspiration, with tones like column white, Rossa Roma and eucalyptus green being some of the many highlights in this offering. There’s a sense of chill around the collection too, with trousers cut more relaxed for some extra room (considering Milan’s heatwave, you’re going to need it) and shoulders slightly deconstructed to soften the power padding. More casual, sportswear-leaning silhouettes also make their way in – a reference to the styles shown in the original 1952 catalogue – through overshirts and suede blouson jackets.
Dunhill delivers a study on effortless British style
Roger Moore, Lucian Freud, and Lord Snowdon all moved through life with their own sharply defined sense of style, brimming with personality, ease, and versatility – sprezzatura, the British way, if you will. It’s this attitude that informed Dunhill Creative Director Simon Holloway’s latest collection, packed with easygoing double and single-breasted jackets and blue sport coats cut in worsted cashmere, while grey linen tailoring pulled from a sharply-dressed noir 1980s London. Tom Guinness’ styling of the collection, showcased in a lookbook lensed by Ethan James Green, spotlights this anthropological study of dressing well, where finishing touches like loose undone scarves mirror those worn by Freud. Because yes, traditional English style has rules, but it’s how you interpret them that carves out your personal style – something Holloway knows all too well.
Qasimi celebrates the life of clothes
For many people, buying and investing in clothing means buying the finished article. Qasimi decided to see things differently in its SS27 collection, looking at garments as an evolving record of gesture, time and transformation. The result is an offering that’s clean and contemporary in silhouette and cut, yet deconstructed and slightly dystopian in the details. Beautifully deep pleats are paired with loose threads, flatteringly cropped jackets constructed out of faded and well-worn fabrics. The natural order of a clothing item’s lifespan is respected and celebrated here. Because the passage of time and the inevitable breaking down of textiles is one that Hoor Al Qasimi sees the beauty in, and so should you.
Tod’s is going off Italian instinct
Sprezzatura. A true defining moniker in Italian fashion, referring to the country’s innate nonchalance when it comes to dressing, and an attitude that translates onto a lot of the defining brands that show at Milan Fashion Week. One of those being Tod’s, which looks within for its SS27 collection, where the true beauty and hook lie in the foolproof effortlessness of it all. The modularity here is key, with great tailoring, simple yet effective shirting and relaxed-in-a-put-together way bottoms promoting easy interchangeability. Accessories round it all off, whether it be the belted leather bags or a keyring that playfully dangles off the belt loop. Opening your wardrobe to these pieces is a cheat code for low-key banger outfits every time, with a playful touch and endless styling options to keep things ticking. Good convenience, and even better clothes.
