From intellectual loafers to pinstripes, Bermuda shorts and nomadic tailoring: discover the SS 2026 menswear trends from Milan Fashion Week Men’s
Spoiler alert: The man of 2026 is on the verge of discovering who he wants to be—though he hasn’t quite figured it out yet. This Milan Fashion Week SS 2026 in menswear didn’t create a dramatic impact; instead, it showcased a maturation of style. Unlike previous editions that felt lukewarm and predictable, something began to shift in menswear trends this year.
Here’s what we observed between Via Tortona and Piazza Affari: the key menswear trends for 2026 that we’ll soon see on the shoulders of the bold…and in the Reels of those who think they’re ahead of the curve.
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Teardrop pleats, shawl collars, and Mediterranean shades took center stage at the Giorgio Armani Spring/Summer 2026 men’s fashion show held at Armani/Teatro
And no, we’re not talking about the usual overcrowded afterparties. Across catwalks and showrooms, a transformation was apparent: less runway spectacle and more emphasis on wearable pieces, classic items with subtle twists, and a broader mix across categories. Modern masculinity has become diverse, softer, occasionally ironic, yet always practical, reflecting the challenges luxury brands face amid broader geopolitical and economic shifts.
Here’s what we spotted between Via Tortona and Piazza Affari: the key menswear trends for 2026 that we’ll soon see on the shoulders of the brave… and in the Reels of those who think they are.
Loafers and Sandals Make a Comeback in SS 2026
Yes, they’re back. Forget those rubber beach slides from 2008. The sandals showcased at Milan Fashion Week SS 2026 come with a stylish pedigree. Prada led the charge by reintroducing flip-flops and toe-ring sandals that echoed the ring-shaped detail on their show invites.
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At Prada men’s 2026 Spring/Summer show in Milan, sandals were showcased that drew inspiration from traditional Indian footwear crafted in select districts of Maharashtra and Karnataka
Loafers also made a comeback—open-toed, preppy, and unapologetically worn with socks. Do they work? Yes, if the rest of the outfit exudes intellectual minimalism rather than giving off a “forgot my shoes at home” vibe.
SS 2026 Pastel Colours: A New Menswear Language
Once again, Prada set the tone with collections staged on shaggy carpets inspired by their iconic SS13 florals. Every outfit, from casual to tailored, played with the four elements—water, earth, air, fire—expressed through a sharp, luminous pastel palette. Pink met red and ochre, while sage flirted with sand.
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Pastel tones at Dunhill’s Spring/Summer 2026 show celebrated the quiet excellence of British craftsmanship, set against the intimate backdrop of Milan’s Giardini Poldi Pezzoli
Dunhill and Istituto Marangoni alumnus Filippo Cascinelli embraced baby blue: the former through sleek SS 2026 tailoring, the latter with sporty headwear and vests. The pastel menswear trend of 2026 strikes a balance between softness and control—think chromatic meditation but with a luxurious twist.
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Snapshot from the SS26 Summer Memories collection by Cascinelli
Stripes and Pinstripes Reimagined for the Modern Man
Vertical, horizontal, and diagonal patterns: it looked like a runway show set in an ethno-chic resort. But no, it was actually Emporio Armani showcasing a return of the (pin)stripe. Even without Giorgio Armani’s presence, the collection radiated timeless elegance.
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Highlights from the Emporio Armani Spring/Summer 2026 men’s fashion show
At Dolce&Gabbana, designers Domenico Dolce and Stefano Gabbana also embraced stripes, reinterpreting the pyjama as a complete outfit rather than just nightwear.
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At the Dolce&Gabbana SS26 fashion show, pajamas transformed into evening treasures, adorned with hand-applied stones and crystal embroidery
David Catalán introduced rave-inspired pinstriped bucket hats and clutches, while Vivienne Westwood drew inspiration from 1920s gangster tailoring, complete with suspenders. The message? Men in 2026 seek order without sacrificing style—that’s why stripes and pinstripes serve as a visual code that balances discipline with freedom, tradition with rebellion, intimate indoor settings with evening extravagance, and Western heritage with global influences.
Nomadic Tailoring: Softness Meets Global Influence
Forget stiff jackets—SS 2026 tailoring is softer, draped, and undone. Giorgio Armani’s collection, titled “Con l’armonia di sempre”, was a love letter to the lightness of summer, showcasing floating silhouettes, double-breasted jackets with shawl collars, and pleated trousers that wrap around the body without constriction.
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Magliano Spring/Summer 2026 collection
Meanwhile, Magliano drew inspiration from cinema, creating an aesthetic rooted in everyday people and places. This approach offers more than just a wardrobe; it invites a rethinking of modern menswear.
The Bermuda Short Returns for SS 2026, with a Twist
Are shorts all that’s on the menu? Not quite. The Bermuda shorts are back. Among the various styles—daring mini shorts, boxers and hot pants—it’s the tailored Bermuda that’s quietly ascending in popularity, reflecting a broader wave of restraint. Its hemline rises modestly just over 2.5 cm above the knee, returning to the body not as a statement of power, but as a clever, knowing gesture.
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Prada Spring/Summer 2026 menswear collection
Vivienne Westwood’s Andreas Kronthaler went oversized and asymmetrical; Paul Smith and Ralph Lauren Purple Label kept it crisp in denim and cotton. Will everyone wear Bermuda shorts? Probably not. But yes, someone will definitely be seen picking up coffee in them.
Sporty Vibes Infused with Soul and Culture in Menswear
MSGM’s “I Feel the Rush” proved that bike culture can be both aesthetically pleasing and a manifesto. Adrenaline met emotional freedom through the use of mesh layers, tech fabrics, and featherlight nylon.
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Look from "I Feel the Rush" collection by MSGM
Mordecai referenced Louise Bourgeois and Uzbek suzani carpets, creating a judo-infused collection with smart proportions and sculpted volume. Meanwhile, Sease, founded by the Loro Piana brothers, transformed Piazza del Quadrilatero into a pop-up tennis club to launch its Tennis_Kit capsule in collaboration with Antonia and Portrait Milano. In this setting, sporty menswear trends evolved to emphasise not just performance, but also presence.
SS 2026 Menswear: Grounded Trends from Milan Fashion Week
Milan Fashion Week SS 2026 didn’t dream big; it dreamed strategically. Or perhaps it didn’t dream at all. Instead, it presented a dose of measured creativity for a market that needs to prioritise sales now more than ever.
The result? A carefully curated selection of commercially viable pieces, enhanced with just enough novelty to feel current. The emphasis was less on bold statements and more on building relevance (and ensuring sell-through).
This season reflects a sense of balance, acknowledging global tensions, changing consumer spending habits, and the need to justify every item produced. Within this measured approach lies clarity: it portrays a vision of a man who knows how to adapt, edit, and remain confident in uncertain times. While this fashion moment may express less in terms of creativity, its significance may be greater than it seems.
Agnese Pasquinelli
Alumna, Milano