Milan Fashion Week SS27: From Jil Sander’s Quiet Complexity to Dolce & Gabbana’s Sicilian Spectacle

It is changeover day across the European fashion capitals—the moment the global fashion press, intrepid buyers, and elite models pack their bags, trade their espresso cups for airport transit, and descend upon Paris. Milan Fashion Week for the Spring/Summer 2027 season officially drew to a close yesterday, September 27, and the momentum has already shifted westward to France. LVMH Prize-winner Julie Kegels wasted no time setting the tone in the French capital, kicking off the afternoon shows with a bang. But before the industry dives headfirst into the final, grueling stretch of the month-long fashion marathon, it is worth taking a moment to reflect on the standout moments, subtle shifts, and unforgettable spectacles that defined the Italian showcases.

While fashion enthusiasts certainly tracked major headlines—such as Prada’s formidable display of 63 distinct skirts—the Milan calendar was brimming with quieter triumphs and eccentric details that easily slipped past casual observers. Did you catch the exaggerated, platformed flip-flops making their debut at MM6? Or Jennifer Lopez channeling a distinct Peaky Blinders aesthetic in the front row at Dolce & Gabbana? If these highlights escaped your radar, a deeper look into the Italian capital’s Spring/Summer 2027 season reveals a week defined by contrasting energies: a return to foundational tailoring, playful subversions of classic garments, and a celebration of rich Italian heritage.

JIL SANDER

At Jil Sander, creative director Simone Bellotti is finally getting his flowers. Since stepping into the role a year ago, the Italian designer has steadily built momentum, quietly winning over critics and commercial buyers alike with each successive collection. His Spring/Summer 2027 presentation easily ranked among the absolute highlights of Milan Fashion Week, proving that Bellotti is successfully putting the legendary label back on the map after a period of being viewed as an underrated industry gem.

This season, Bellotti leaned heavily into the core concept of minimalism that defines the Jil Sander DNA, yet executed it with a level of intellectual depth that separated his work from mere basic dressing. On the surface, the clothes appeared remarkably simple, clean, and restrained. However, upon closer inspection, the garments revealed an incredible degree of complex, meticulous design. Fabrics fell effortlessly and fluidly across the body, belying the sophisticated engineering beneath. Every piece was cleverly pinched, gathered, and tucked to construct precise, bespoke silhouettes that challenged the eye while maintaining absolute ease of wear.

FENDI

Guests arriving at the Fendi show were given explicit instructions to immerse themselves in the atmosphere before a single model hit the runway: they were encouraged to dance on their way into the venue. High-profile celebrities, including Rachel Zegler, Iris Law, and Maisie Williams, were spotted letting loose within the show space, grooving to classic Italo tracks before taking their assigned front-row seats.

The venue itself had undergone a radical transformation, converted into a giant, mirrored box directly inspired by Italian sculptor Luciano Fabro’s famed Cubo di Specchi (cube of mirrors). The architectural choice forced the audience to stare back at their own reflections, creating a disorienting, immersive environment where guests caught warped, fragmented glimpses of the collection passing by.

Matching the vibrant energy of the soundtrack—which brilliantly blended Adriano Celentano’s nonsensical rhythmic classic “Prisencolinensinainciusol” with Raffaella Carrà’s driving anthem “Rumore”—the collection emerged as a fascinating study in unexpected pairings. Stilettos were deliberately styled with casual socks, baggy, relaxed-cut jeans were juxtaposed against 18th-century-style frock coats, and delicate, sheer camisoles were accessorized with bold cheetah-print chokers. It was a masterclass in high-low styling that honored Fendi’s historical penchant for theatricality.

MM6

As Maison Margiela’s playful, undone younger sibling, MM6 approaches its upcoming 30th anniversary next year with an absolute refusal to grow up. The diffusion line proved this season that advancing age has not dulled its youthful, mischievous, and anarchic spirit.

The show began with an immediate burst of subversion when two MM6 employees, dressed uniformly in their crisp white lab coats, literally tore open the heavy paper entrance to the runway. The very first look set a tongue-in-cheek tone: a pair of standard trousers cleverly transformed into a mini dress, featuring a fly left wide open to reveal the model’s bra underneath. This logic of anatomical and sartorial confusion continued as shirts were repurposed as dresses and traditional jackets were strapped on to function as skirts.

Echoing the topsy-turvy, deconstructivist design worlds championed by contemporary labels like Hodakova and Zomer, the MM6 Spring/Summer 2027 collection was built entirely on the premise of flipping convention and reversing expectations. The footwear, in particular, emerged as a major talking point. Created through an unexpected collaboration with Havaianas, the collection featured platformed flip-flops stacked mile-high with tiered foam soles, alongside pairs meticulously cut to follow the individual shape of each toe. It is a safe bet that these sculptural sandals will dominate fashionable beaches come next summer.

ARMANI

Just over a year has passed since the passing of the late, legendary Giorgio Armani at the age of 91, yet the iconic brand continues to operate at the absolute peak of its powers, doing what it has always done best: delivering sleek, sharp, and uncompromising tailoring.

Under the creative direction of Armani’s niece, Silvana Armani, the Spring/Summer 2027 collection embraced bold 1980s silhouettes, featuring dramatic, structured shoulder pads on double-breasted suits that were styled with nothing worn underneath. Despite being accompanied by a sleepy, atmospheric jazz soundtrack, the collection undeniably shouted nightlife—evoking the kind of effortless nocturnal glamour that Grace Jones famously encapsulated in her anthem “Nightclubbing.”

Meanwhile, a significant transition is quietly afoot at the brand’s more accessible sibling label, Emporio Armani. Rather than staging a traditional runway show this season, Emporio Armani released a comprehensive lookbook, effectively closing out a chapter with a neat, simple, and back-to-basics approach before ushering in an entirely new era. The Spring/Summer 2027 offering marks the final Emporio collection designed collaboratively by Leo Dell’Orco and Silvana Armani. Next season, the creative reins will officially be handed over to Dario Vitale, who departed Versace late last year following the Prada Group acquisition.

DOLCE & GABBANA

Travelers who tuned into the second season of HBO’s The White Lotus will easily recognize the picturesque Sicilian town of Taormina. By sheer coincidence, while on a road trip across Sicily earlier this summer, one traveler arrived in Taormina on the exact day that Dolce & Gabbana had completely overtaken the municipality. A massive, all-black D&G superyacht bobbed peacefully in the harbor, while the ancient streets overflowed with international models, each identifiable by a distinguishing number tied around their waist. Inside the historic, 2,000-year-old Greek amphitheater, production teams were hard at work preparing for that evening’s exclusive Alta Moda fashion show, which included a star-studded performance by Jennifer Lopez.

Last week in Milan, Dolce & Gabbana successfully transported the fashion crowd back to that sun-drenched Sicilian atmosphere with a collection aptly titled STRAVAGANZA SICILIANA. Jennifer Lopez made another appearance, this time spotted commanding the front row dressed in a 1920s-style suit and a flat cap—an ensemble that immediately drew widespread comparisons to Cillian Murphy’s character in Peaky Blinders. Few designers would dare to suggest that gritty Birmingham and sun-drenched Sicily share a common thread, but at Dolce & Gabbana, such eclectic cultural collisions are executed with unmatched theatrical flair.

MAX MARA

An intriguing cultural phenomenon is currently unfolding around Max Mara: Generation Z has discovered the brand. Founded more than 70 years ago and historically renowned for its 1990s minimalism and Phoebe Philo-level aesthetic effortlessness, the Italian house has unexpectedly emerged as a viral heavyweight on resale platforms like Vinted and Depop throughout 2026.

While Max Mara has always remained a steadfast pillar of Italian luxury, it is undeniably experiencing a robust renaissance. This newfound popularity among a younger, digitally native demographic means that unprecedented levels of attention are now trained on its runway presentations—such as the formidable show the brand just mounted at Milan Fashion Week.

This season, British designer Ian Griffiths zeroed in on one of the brand’s foundational design pillars: utility luxe. The resulting collection was anchored in earthy beige tones, heavy canvas textures, and sharp military-inspired silhouettes. Waists were cinched securely with chunky leather belts, extra utility pockets were seamlessly integrated into cotton gilets, and stiff collars were persistently popped, standing rigidly to attention.

At Sportsmax, Max Mara’s younger, more experimental contemporary arm, the design team chose to reflect the stark realities of our current climate. Literally addressing the severe heatwaves that have repeatedly plagued Europe over recent summers, Sportsmax offered a pragmatic, high-fashion answer to extreme weather dressing: simply remove the sleeves from your coats.

TOD’S

Tod’s traces its corporate lineage back to a humble shoe-cobbler workshop operating in 1920s Italy. More than a century later, the brand’s institutional loyalty to master craftsmanship remains as absolute as it was the day it first opened its doors, matched only by its unwavering devotion to luxury leatherwork.

An obsessive attention to detail is woven directly into the company’s DNA. For its Spring/Summer 2027 presentation, Tod’s stayed entirely true to these historical foundations while injecting a fresh, contemporary sporting edge into the lineup. The collection possessed a distinct, confident masculine energy—featuring boxy suit jackets paired with even boxier shorts—punctuated by vibrant injections of coral, mustard, and crimson color-blocking.

The quintessential Tod’s woman for Spring/Summer 2027 is envisioned as someone who effortlessly plays a competitive game of morning tennis before spending the afternoon commanding the boardroom as everyone’s boss. The mood was underscored by Anna Wintour, who observed the proceedings from the front row as top-tier models Awar Odhiang and Mariacarla Boscono breezed effortlessly past.