If there’s one thing to count on during Fall/Winter fashion week, it’s that the calendar is stacked from January to March. While pre-season menswear shows were once treated as a lead-in to February’s three (and a half) weeks of ready-to-wear, January’s menswear-oriented runways have taken center stage in recent years—a welcome expansion. Men’s fashion has only become more exciting as creative directors have played their usual game of musical chairs, seeing Miuccia Prada collaborate with deconstructionist Raf Simons for her eponymous Milanese brand, and Sabato De Sarno now at the helm of Gucci post-Michelefication. These joint efforts are invigorating, laying the groundwork for a stunning season.

After touching down in Milan last week, Document Journal shares its roundup of the best and brightest Men’s Fashion Week shows from the heart of the Italian fashion capital.

Prada

If a svelte man with an office job (and an affinity for bespoke millinery) stepped outside of his tiny gray cubicle to find the wonders of the great outdoors, he’d be wearing this season’s Prada. Miuccia Prada and Raf Simons showcased their latest sartorial line in Fondazione Prada, which the creative directors bedecked with cubicles in a natural landscape, a scene meant to represent the act of going from inside, to outside. The brand’s press release described this uncanny conflation as “demonstrating the paradoxical dichotomy between these two coexisting worlds.” But even in this new reality, the classic Prada talismans were all there: the ties were skinny, the pants somehow skinnier, and the oxford shirts were tucked in with one (sometimes two) belts. As usual, one unexpected and dapper element surprised: this season, it was the hats. Military-inspired swimming caps in Crayola colors were styled like little cloth skull caps, as were shiny leather-topped headpieces reminiscent of the ’80s New Wave movement. The duo has yet again proved itself adept in the dark arts of creating a singular perspective that’s equal parts each designer: in the case of this season, Ms. Prada’s iconically to-the-point styling tendencies dovetailed with the oh-so-sought-after Raf sweaters. Prada’s Fall/Winter 2024 menswear show explored human nature by showing audiences how we react to human-made and organic environments, always seeking connections to something greater.

Zegna

Scientists may have proven heliocentrism; however, the center of Zegna’s universe this season is cashmere. In a show titled “In the Oasi of Cashmere,” creative director Alessandro Sartori constructs what he calls an “open system made of elements that can be layered and combined in many ways.” Freedom comes from the potential to see different ways of arranging the garments, each styled in monochromatic looks in bianco, ghiaccio, and foliage brown, to name a few. The double-collared blazers, generously-tailored trousers, and boxy anoraks adapt to a breadth of body postures as well as attitudes, as seen on famed cool-guy musician James Blake, a friend of the house who provided a live score for the runway event. Built on both evolution and adaptation, Zegna’s latest men’s season places the creativity of getting dressed on its well-deserved pedestal.

Fendi

Silvia Venturini Fendi draws from both the town and country “for fresh air and even fresher ideas,” as written in the show’s press release. This season, Fendi kept it classic with a theme grounded on duality—suede coats with shiny leather Peter Pan collars, neutral palettes of greens and browns juxtaposed with deep, brooding maroons. The footwear consisted of rich-looking Wellingtons and boat shoes, broaching high fashion with more relaxed daywear silhouettes. Overall, the runway show was not only dynamic but well-considered—less anchored in the label’s iconic inward-facing F’s than in the luxury of simple matching elements, like dramatically ribbed tan corduroy pants paired with an equally ridged maroon leather doctor’s bag. The sophistication of the accessories line is an ultimate tribute to the twoness that unifies the collection, debuting the Siesta bag, which flattens into a pillow, and the Melon hobo, a pocketbook shaped by intricate folds, which can be rearranged for different desired looks. Shifting between fashion and architecture, urban and rural, day and night, this season’s Fendi provides a Roman twist on the classics.

Gucci

Sabato De Sarno’s Gucci-impact is manifold. Last September, the self-described fashion elite had qualms about becoming the legendary label’s new creative director—yet in the end he decided there was a place for his vision, telling Vogue that he doesn’t care about the Instagram moment, but rather the design process itself. This sentiment manifests in the mindful proportions of each garment: odd to the luxury shopper looking for a viral moment, but deliciously impractical (that is, perfect) for the fashion aficionado looking to stun. Highlights included a buttonless blazer ribbed at the sides as if with fabric gills, a chic duster that looks like an extra-long stole, and a burgundy full-GG-print suit with a palm-length glove of the same pattern. De Sarno reminds us of the everyday whimsy luxury garments can offer, especially when canonically inspired (the use of the all-over logo referencing Tom Ford) and cut well (suiting played an integral role in the synergy of the collection). Among a sea of buttery leather overshirts with matching satin ties and a range of instantly classic accessories, the tailored looks were perhaps the strongest: such as a burnt sienna vinyl-looking number featuring a marvelous padded-lapel coat and matching trousers, for example. Indeed, De Sarno’s Gucci follows in the footsteps of the many great creative directors before him: it puts fit first.

Brioni

With deep roots in Italy’s Abruzzo region, the fashion world would be hard-pressed to find a label more resolute in its commitment to the history of its craft. Norbert Stumpfl, the innovative force behind today’s Brioni, keeps this legacy in mind as he charts new sartorial paths forward. The brand’s latest presentation displayed the traditional tenets of men’s suiting, overtly tailored and creating in “a realm for research, self-expression, and aesthetic sensibility,” according to the press release. Knits feel nimble in their weight, whether worn with the sleeves rolled up or tied around the neck, and the slim trouser and fitted jacket suit separates are intrepid in their dedication to impeccably tailored ease. Tweeds, leather, and wool merino: for Brioni, these are the simple makings of a cohesive, opulent presentation that treats precise garments as its pillar.

JW Anderson

It’s fitting that JW Anderson’s Fall 2024 runway finds its roots in Eyes Wide Shut, a landmark Stanley Kubrick film. The central tension in the film lies in the interplay between wealth, conservatism, and discreet erotica, in which the characters are slowly drawn into darkness behind closed doors. As a designer, JW Anderson is rooted in similar anglicisms to never be outwardly sexy, and so the film’s influence on the garments is never forced. Throughout the collection, Anderson utilized deep reds on oversized silhouettes, draped to show just the right amount of skin. Regardless of gender expression, models wore sheer black tights over panties, a choice that transformed audiences into voyeurs of sorts, watching a private moment instead presented for a room of hundreds. Reinterpretations of moccasin boots, large cat sweaters, and the latest iteration of the zipper tab (a detail giving a bit of lip service to a more tasteful influencer set) served as little oddities as considers as the designer’s larger pieces, again mirroring Kubrick in his technical perfectionism. With the last few collections, perhaps Anderson has initiated the next generation of fashion mastery.