Milan Fashion Week S/S 2026: Defining Moments

Milan Fashion Week has never been short on spectacle, but this season feels like a defining chapter.

The city is alive with first-time creative director debuts, heartfelt farewells, and an unmistakable vibrancy that reinforces Milan’s standing as one of fashion’s most vital destinations. From Demna’s restrained Gucci introduction to Louise Trotter’s eagerly awaited Bottega Veneta presentation, Spring/Summer 2026 is shaping up to be a season etched into memory.

The week officially began on 23 September with Demna’s quiet Gucci unveiling – not on the runway, but through The Tiger, a short film directed by Spike Jonze and Halina Reijn, teasing his subversive direction for the house. The following day, Simone Bellotti took the helm at Jil Sander, marking a new era after Luke and Lucie Meier’s ten-year reign. Later, Dario Vitale – formerly at Miu Miu – made his Versace debut in an intimate, charged show. Most recently, Louise Trotter revealed her perspective for Bottega Veneta, one of the rare female appointments in the sweeping creative changes of 2025.

This season balances reflection and reinvention. As new voices take charge of iconic maisons and the city prepares a tribute to Giorgio Armani’s incomparable legacy, S/S 2026 highlights Milan’s dual role as both custodian of heritage and engine of innovation.

In essence, Milan isn’t simply hosting shows this week – it’s shaping history.

The excitement comes tinged with sadness too: the fashion world prepares to bid farewell to Giorgio Armani, who passed away earlier this month at 91. His legacy will be celebrated in a closing tribute show – a fitting finale to a career that defined Italian fashion.

Let’s look at the standouts of the week.

Dolce & Gabbana

On Saturday, the Metropol Theatre became the stage for a surreal high-fashion pyjama party, blurring the lines between runway and cinema. The cast of The Devil Wears Prada sequel – Meryl Streep, Stanley Tucci, and rising star Simone Ashley – sat in character in the front row, sparking excitement and even coaxing a rare smile from Anna Wintour.

On the catwalk, Dolce and Gabbana extended their menswear “Pyjama Boys” into womenswear. Crystal-encrusted striped sets, sheer robes, and lace bodysuits brought sensual energy, while footwear swung between plush slippers and towering stilettos. With Meryl-as-Miranda Priestly nodding in approval, the duo delivered a show that was both theatrical and true to their signature style.

Versace

Dario Vitale’s first collection for Versace took over the Pinacoteca Ambrosiana, transformed into the remnants of a wild night – unmade bed, scattered glasses, overflowing ashtrays.

The clothes echoed the mood: plunging-back mini dresses exposing lingerie, brightly hued oversized tailoring, and metallic chainmail pieces interlaced with baroque motifs. Vitale avoided literal archive nods, instead channeling Gianni’s rebellious spirit. “It’s about the feeling of Gianni, the legacy of Versace, not just the clothes,” he said backstage. The result was daring yet reverent – a bold step forward for the house.

Max Mara

Ian Griffiths turned to Madame de Pompadour, Louis XV’s witty and influential muse, for his S/S 2026 collection “Rococo Modern.”

The runway blended 18th-century grandeur with contemporary pragmatism: trench coats with dramatic flared sleeves, organza petals scattered over dresses, and brocades softened by clean tailoring. Hair pulled back with black bands nodded to Pompadour’s style, while silhouettes balanced historic flair with modern clarity. It was Max Mara at its sharpest – intellectual, wearable, quietly powerful.

Prada

Miuccia Prada and Raf Simons’s latest womenswear collection at the Fondazione Prada explored the tension between uniformity and individuality in today’s algorithm-driven world. Stripping back the set to a stark orange-lacquered floor, the designers framed their vision around the idea of the uniform, reimagined as a source of protection, neutrality, and even elegance. Structured shirts and pleated trousers met playful details like jewel-toned earrings and mock-croc handbags, while flashes of glamour—opera gloves, crystals, and sculptural taffeta—broke through the sobriety. Skirts spliced with ruffles and pleats, as well as draped tops, embodied the designers’ pursuit of “shape without structure.” Ultimately, the collection embraced adaptability and autonomy, offering women the freedom to compose their own identities through clothing, moving away from rigid forms toward a vision of liberation both physical and psychological.

Fendi

Silvia Venturini Fendi’s second season leading both men’s and womenswear radiated optimism and play. With Marc Newson’s colorful block seating as the backdrop, the collection evoked a “future summer” that was both nostalgic and forward-looking.

Sportswear dominated: pleated skirts reimagined with toggles, translucent sweatsuits trimmed in shearling, oversized woven totes in bold hues. The beloved Peekaboo bag returned, this time with a sparkling sequined lining. The collection captured Fendi’s talent for fusing joy with sophistication.