If Milan Men’s Fashion Week SS27 proved one thing, it’s that menswear is no longer playing it safe. This season, designers moved away from the mundane, presenting sensational collections imbued with unexpected palettes and eye-catching elements that pushed the boundaries of what menswear looks like in the coming season. The runways were awash with personality, proving that getting dressed can be both expressive and effortless.

Against Milan’s sweltering summer backdrop, the collections celebrated everything Italian fashion does best: impeccable craftsmanship, timeless elegance, and an unwavering commitment to reinvention. The result? A season that made a compelling case for where menswear is headed next.

Here are six collections that completely stole the show for me.

Ralph Lauren

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There’s something refreshing about the American influence on the Italian fashion scene, particularly with Polo and Ralph Lauren Purple Label. Purple Label, in particular, stood out for impeccably tailored formalwear featuring elegant beige suits, sophisticated pinstripes, and dapper accessories such as sunglasses and berets. One of the collection’s biggest highlights was a limited-edition collaboration with Japanese label Kuon, where indigo longline coats adorned with traditional sashiko embroidery brought together American heritage and Japanese craftsmanship in a seamless, thoughtful dialogue.

Polo Ralph Lauren returned with classic collegiate styles – varsity jackets, polo shirts, and baseball caps – evoking a vibe that many of us grew up watching on our screens or experiencing. Rooted in Ralph Lauren’s signature Americana, the collection reimagines the modern gentleman through classic tailoring, easy separates, and understated luxury.

Thom Browne

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Thom Browne’s debut show in Milan stayed true to its unmistakable design language while introducing fresh twists on its signature tailoring. Building on its iconic tailoring, the collection introduced playful reinterpretations through kilts, Bermuda trousers, and Edwardian-inspired styling, complete with low V-neck cricket knits, straw boater hats, impeccably cut jackets, and whimsical deckchair stripes.

Adding a touch of whimsy, Thom Browne embellished outerwear and accessories with intricate bee and floral motifs, softening the collection’s sharp tailoring. Described by the designer as “an evolution of his core identity,” the collection felt both unmistakably Thom Browne and refreshingly new.

Prada

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Titled “Clarity,” Prada’s SS27 collection, designed by Miuccia Prada and Raf Simons, made a compelling case for stripping menswear back to its essentials. Rejecting excess in favour of clean lines and purposeful design, the collection explored the idea that simplicity can be just as impactful as embellishment. As you delve into it, you’ll notice how it balances style and functionality.

Signature wardrobe staples like jeans, jackets, and t-shirts were reimagined through Prada’s unmistakable lens, with cropped proportions, slim silhouettes, and sharp tailoring lending everyday pieces a renewed sense of sophistication. Structured denim, supple leather, and muscle-fit knit vests featuring geometric motifs brought texture and dimension, while airy translucent fabrics offered a lighter contrast. Colour schemes shifted from monochrome neutrals to deep burgundy, punctuated by unexpected flashes of neon yellow and scarlet red. Finishing touches came in the form of structured pouch bags worn on utility belts, reinforcing Prada’s vision of functional dressing with a distinctly modern edge.

Dolce & Gabbana

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With “Vacanze Siciliane,” Dolce & Gabbana looked beyond postcard-perfect imagery to capture the essence of Sicily through craftsmanship, culture, and character. Rather than relying on clichés, the collection translated the island’s rich visual language into a wardrobe of distinctive colours, textures, materials, and silhouettes that felt unmistakably Dolce & Gabbana.

Opening with Nero Sicilia, the house’s signature expression of Sicilian black, the collection grounded itself in sharp tailoring before giving way to the vibrant hues, artisanal embellishments, and sun-soaked glamour of a Mediterranean summer. The collection unfolded like a journey across the island, following an imagined traveller whose wardrobe evolved with every stop. Echoing Sicily’s landscape, the palette moved through sandy neutrals, limestone whites, sea blues, and pistachio greens, with shades inspired by the island’s iconic granita adding a distinctly Mediterranean freshness to the collection.

Paul Smith

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On the runway, Paul Smith redefined tailoring with a fresh, effortless twist, featuring unlined, lightweight pieces and eliminating heavy shoulder padding. Fabrics like silk and silk-cotton were meticulously washed or dyed for a relaxed sophistication, resulting in a stylish yet easygoing wardrobe.

Highlights included an iconic jacket with a striking lapel, reimagined in a single-breasted silhouette, emphasising comfort without sacrificing elegance. The show showcased silky fabrics paired with loose trousers and quirky fishing lures as boutonnières. With nods to the 1990s and collaborations with emerging talents, the collection reimagines the men’s suit, moving beyond rigid corporate norms into a realm of expressive style.

Giorgio Armani

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Leo Dell’Orco and Silvana Armani concluded the season with a captivating showcase at Palazzo Orsini in Brera, embracing the timeless elegance championed by the late Giorgio Armani. The collection featured a serene palette of navy, grey, and earthy tones, complemented by collarless jackets and lightweight silk trousers that evoke a relaxed Mediterranean vibe.

True to form, the label steered clear of fleeting trends – those ultra-slim silhouettes and vibrant colour explosions that seem to dominate the fashion scene. Playful accessories, like attractive brooches and woven bucket hats, added a refreshing spirit to the summer ensembles. This collection beautifully pays homage to Armani’s vision of sun-soaked living, embodying the effortless sophistication that defines his legacy.