(L-R) Giorgio Armani; Prada; Zegna; Emporio Armani

IT’S A STRANGE THING to be in the middle of summer while observing the autumn-winter 2025 menswear collections currently rolling out in Europe. Yet here we are, watching on from the Esquire office as the biggest brands in menswear send coats and knits down the runway.

Milan fashion week is currently underway (while concurrently the US Presidential inauguration of Donald Trump is happening in Washington D.C.), and we’ve seen designers like Giorgio Armani and Alessandro Sartori at Zegna make a case for spacious tailoring in draped, heavy fabrics. Muiccia Prada and Raf Simons were a highlighted marquee event. Their object-cum-invitation of choice this season? A pipe bearing the Prada name, which alluded to their runway reinforced by scaffolding, designed by Australia’s own Catherine Martin. Though the collection was anything but industrial, contrasting plaids with raw-edged leather and furs, as a nod to the power of feeling over the formulaic.

Now, as the fashion press, famous brand ambassadors (keep an eye out for the Oscar-hopefuls courting brands – many will be wearing these looks to the awards shows in March), and buyers make their way from Milan to Paris, scroll on to read our thoughts and opinions on the autumn-winter 2025 season so far.

Giorgio Armani

Photography: courtesy of Giorgio Armani

Carried through from the Emporio Armani show that happened this past Saturday, the Giorgio Armani show reaffirmed that Mr. Armani is feeling his velvets. But then again, is he ever not? While the Emporio offerings saw the fabric in toxic chartreuse and jewel hues that raged on about desire and seduction, at Giorgio – the pinnacle of the Armani empire – luxurious velvets were distilled into separate colour sections of grey, green, red, blue, and greige for the everyday. Velvet’s sheen and drape accented the overall louche feeling of the tailoring: buttons on jackets not wholly done up, neckerchiefs and silken scarves left loose to drape around the neck. 

And if there’s a body part du jour for this menswear season, let it be the neck. The high sheen of the silk and velvet scarves aren’t there to keep you warm – here matching with the colour of the ensemble – only to top off the fit like a shiny cherry on a sundae. It’s an accent of delight.

Vintage Armani is a robust corner of fashion resale sites right now, and one wonders whether Mr. Armani is aware of tapping that vein, seen in the loose loden-wool trousers with pinstripes, herringbone, and, again, velvet. A return to stylish airport fits of the ’90s? Worn in leather moto jackets and gloves paired with parachute and cargo pants tucked into laced up boots – for the stylish motorcyclist around Milan’s dry winter? Cardigans and gilets (top button only) signalled jackets and tailoring to be worn on the boxy side; enough allowance for layering. By the end were seven his-and-her looks for the evening where velvets were inky and wools were deeper. But the playful knitwear remains, with accented crystal hems to mirror that of his companion for the night. – Tyler Dane Wingco

Photography: courtesy of Giorgio Armani

Zegna

Actor John Turturro makes an appearance on Zegna’s autumn-winter 2025 runway – older men are in! Photography: courtesy of Zegna

Sprezzatura, or ‘studied casualness’, is the very essence of Italian fashion. It’s also something Alessandro Sartori explores with for Zegna’s autumn-winter ’25 collection, exemplified most succinctly in look 47, modelled by actor and filmmaker John Turturro, a shearling-collar raglan sleeved overcoat, layered with a navy v-neck and two collared shirts. (Turturro is currently on a press tour for season 2 of Apple TV’s Severance; this runway is a fitting platform to promote the office drama.) Perfect casting, considering that finally, older men are having their menswear moment; they are experts in the art of wearing clothes with attitude after all, and our so-called youth-obsessed society couldn’t be more obsessed.

Other questions proposed by this impressive show: how exactly can a well-worn suit look effortless? And how to carry oneself in an overcoat that sways well below the knees with ease? (The patina of well-made clothing has become aspirational, accelerated, no doubt, in our fast fashion world.)

Such styling notes make a case for swagger coming with age, seen elsewhere in the boggling eyewear that dangles on a chain, bumping off the chest as the models walk. Other styling notes included popped lapels and collars big enough to shield the face (from pulverising wind or from leering eyes); the width of the lapels and collars are also skewing wider this season. – Tyler Dane Wingco

Photography: courtesy of Zegna

Prada

Photography: courtesy of Prada

In today’s ordered world, where everything is learned and structured and set out in front of us, choosing to shun premeditation in favour of listening to your instincts is a radical act. This season, Prada co-creative directors Miuccia Prada and Raf Simons indulged in that very human brand of radicalism, completing a look not when all the boxes were ticked and the brief was fulfilled, but when it felt ‘just right’. It’s amazing, really, the levels of creativity gut feelings can produce, because while the materiality of this collection was more eclectic than their recent outings – tablecloth-spec 70s floral prints were layered beneath raw-edged pelts – it was the presence of the human hand and brain that tied it up in a coherent bow. That, and the scuffed-toe cowboy boots, which came in a suite of patterns and colours. – Amy Campbell

Tod’s

Photography: courtesy of Tod’s

Set within curated vignettes photographed in Villa Necchi’s modernist salons of cold metal and marble, auburn wood and mustard carpeted floors, Tod’s released its autumn-winter ’25 collection in homage to Italian architectural crafts. Innovations in leather – the brand’s centrepiece – were a focus for Matteo Tamburini, who introduced his Pashmy project this season. The new Pashmy leather is made from soft, silky, lightweight leather that draped and crunched into delicate shapes – like a pashmina (after which it is named) flailing in the wind. The structural composition is observed best in the supple Nappa leather and suede outerwear that alternate in cut between slim and voluminous, though still big enough for layering and comfortable movement. 

Ankle boot, desert boot, and loafer variations of the Gommino were a main showcase on the footwear front, brushed by the brand’s artisans to a casual sheen. But it’s the Di Bag Folio that’s perhaps the centrepiece for what Tamburini hoped to achieve this season. Versatility and Italian casual style are the intent in styling, and the capacious bag that’s big enough for the office to the gym to the plane (not in that order) is constructed as a boxy carry-all with supple suede. It’s that structured softness Tamburini is looking for. – Tyler Dane Wingco

The Di Bag Folio sees the structure and softness designer Matteo Tamburini hoped to achieve in the collection. Photography: courtesy of Tod’s

Emporio Armani

Photography: courtesy of Emporio Armani


‘Seductive’ was the title of this Emporio Armani collection. Read the show notes: “to seduce is to draw others in, to captivate. Seductive is the master of this subtle art, practised with words, gestures and style.” This season, the Emporio Armani man seduced us in waves, beginning with the sporty and functional, then progressing into his polished, bookish self, before finishing with his most luxurious version. Totalling 111 looks, it was an odyssey through the house’s codes and silhouettes; a reminder that variety is often the most seductive thing in life. – Amy Campbell

Dolce & Gabbana

Photography: courtesy of Dolce & Gabbana

The word paparazzi became popular thanks to Federico Fellini’s 1960 cult classic film La Dolce Vita, but never has the act of capturing and consuming candid images of celebrities going about their days been more relevant than today. So, a pit of papping photographers formed the backdrop to Dolce & Gabbana’s autumn/winter 2025 men’s collection, lighting up a procession of looks capable of making anyone feel like a celebrity. While blue denim accents felt appropriately off-duty, it was the coats – fur, leather, fur and leather – that made it feel like a collection for those who want to be noticed, even if they’d prefer the masses to think otherwise. And if the first half of the collection was for the day, the latter part was designed for the red carpet, where double-breasted tuxedos adorned with 1940s-inspired brooches brought an air of Hollywood glamour. – Amy Campbell


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