Attending Milan Fashion Week for the very first time transforms the entire experience into something extraordinary. From the grand runway productions and the vibrant local culture to the world-renowned cuisine, every single hour feels as though something exciting and unexpected is waiting just around the corner. Yet, there is also a comforting familiarity that seasoned fashion week attendees come to expect—the rhythm of back-to-back shows, intimate re-see appointments, late-night dinners, and hurried coffee chats between venues. Somehow, Milan managed to continually surprise and delight, avoiding any sense of a repetitive routine. Instead, the city, the visionary designers, and the stylish attendees generated a buzzing, electric energy that powered daily schedules from morning until late into the night.
The journey through the Spring/Summer 2027 season unfolded with all its vivid details, capturing the essence of one of the fashion calendar’s most thrilling weeks.
Monday, September 21: Arrival and Ease
The journey began with an arrival in Milan around 11:00 AM, leading straight to the designated home for the first three days of the trip: the AC Milano Hotel. After a quick refresh, unpacking, and a much-needed coffee to energize the afternoon, the schedule immediately kicked into motion. Travel days inevitably take a toll, resulting in chipped nails that required a quick fix at a nearby salon.
With grooming settled, the afternoon involved taking care of laptop work and various meetings before heading out for a welcoming dinner with Editor-in-Chief Faith Xue at a local restaurant. It provided an ideal, gentle transition into the whirlwind of fashion week madness, setting a calm tone before the intense schedule of shows began.
Tuesday, September 22: Clubbing Couture and Behind-the-Scenes Access
Tuesday morning started with a refreshed mindset, dedicating the early hours to catching up on digital correspondence and laptop tasks before getting dressed for the very first major show of the season: Glenn Martens’ final presentation for Diesel. As widespread social media coverage quickly confirmed, the runway transformed into an immersive sex club environment, offering a brilliant introduction to the unpredictable nature of Milan Fashion Week.
The atmosphere grew intensely provocative; an attendee seated right next to the press section began passionately kissing neighboring guests while loud, simulated moans echoed through the speakers and the collection grew increasingly raunchier. Capturing the mood backstage, pop artist Kim Petras encapsulated the collective sentiment, remarking, "Everyone is feeling horny!"
Following the sensory overload of the Diesel show, a quick return to the hotel allowed for a fast outfit refresh before heading over to the Off-White offices. There, the team filmed an installment of the "Clothes Call" series featuring Olandria, documenting her official fitting for the brand’s upcoming 10×10 Celebration alongside her stylists, The Reismans. The collaborative energy and warmth among the team offered a fascinating look at the behind-the-scenes mechanics of high fashion. The evening concluded with Faith Xue joining for a late-night dinner at Da Bolognese, where the day’s events were capped off by sharing a traditional tiramisu.
Wednesday, September 23: From Jil Sander’s Hype to Ralph Lauren’s Grandeur
Wednesday marked one of the most intense and jampacked days of the entire Milan itinerary, kicking off early with the highly anticipated Jil Sander presentation. Anticipation had been building across the city for days, and the physical presentation in the brand’s showroom completely lived up to the massive hype. Packed-in attendees crowded to witness a masterclass in textures and shapes, featuring a collection defined by crinkled fabrics, soft pastel hues, and dramatic, billowing silhouettes that immediately positioned it as a contender for favorite collection of the season.
From Jil Sander, the schedule required a swift dash to the Antonio Marras show, hosted within the picturesque setting of the Giardino Vincenzo Muccioli. Models gracefully wove through a meticulously styled dinner party scene, culminating in a deeply dramatic and theatrical reunion between a bride and groom that captivated the entire audience.
Next came the Ralph Lauren re-see at the opulent Palazzo Ralph Lauren, offering an up-close and personal examination of the Spring/Summer 2027 collection. The intricate embellished detailing and luxurious fur-trimmed garments revealed even more depth and craftsmanship upon closer inspection, leaving a lasting impression—particularly a standout gold top that remained a talking point long after leaving the room.
As the sun began to set, the evening transitioned into the Brunello Cucinelli preview, immersing guests in the understated, refined world of classic Italian elegance. This was followed by a quick pop-in to celebrate the official store opening for The Frankie Shop. Having worked up a considerable appetite from the day’s constant movement, the evening wrapped up with a long-awaited dinner reservation at Gloria Osteria Milano, enjoyed alongside the talented team from KCD.
Thursday, September 24: Nostalgia, Cavalli Grunge, and Intimate Dining
Thursday brought another relentless schedule, with each scheduled appointment feeling more thrilling than the last. The morning began with a first-ever attendance at the Max Mara show, held inside the grandiose and historic Palazzo del Ghiaccio. The collection offered an array of impeccably tailored, elegant everyday garments that glided down the runway. Adding a delightful touch of personal nostalgia, a mini Gossip Girl reunion unfolded in the front row, warming the hearts of 2000s television fans.
Immediately following Max Mara, consecutive re-see appointments for Jil Sander and Prada allowed for a deeper appreciation of the garments. The intricate construction and minute design choices solidified both houses as seasonal favorites, with Prada’s daring bra tops sparking immediate debates over personal styling choices and wearability.
After completing the re-see appointments, luggage was transferred to a new Airbnb rental ideally situated in the bustling Duomo area. The location won immediate affection, celebrated by brewing a fresh coffee and stepping out onto a private balcony overlooking the iconic Duomo cathedral.
Energized by the new surroundings, the afternoon continued backstage at Roberto Cavalli, where unadulterated Y2K aesthetics reigned supreme. Leopard print, exposed undergarments, and towering heels dominated the styling, complemented by messy, post-skin-care hair and shimmering eyeshadow. Watching the collection hit the runway confirmed a cohesive mood defined by unbridled sex appeal, nightlife culture, and effortless grunge.
The evening progressed to a serene walkthrough of the Emporio Armani presentation, where a sequined cummerbund caught the eye as a standout styling detail. The night concluded at Don Carlos, an intimately scaled restaurant featuring just eight tables, where an exquisite multi-course meal offered a refined take on traditional Italian cuisine alongside unexpected culinary creations, ranging from delicate tortellini in rich broth to an inventive sea bass Wellington.
Friday, September 25: Tod’s, Blumarine Playfulness, and The Attico
Friday morning commenced at the Tod’s presentation, providing an opportunity to chat with notable attendees Kelly Rutherford and Diane Kruger before taking a front-row seat. The Spring/Summer 2027 offering successfully bridged two seemingly disparate worlds, blending sexy swimwear silhouettes with highly wearable leather garments in a combination that proved surprisingly cohesive on the runway.
From Tod’s, the afternoon involved filming a Show Day diary alongside Ivy Getty for the Blumarine presentation. Upon arrival, an accidental run-in with Olandria—who made a striking statement in a sleek bodysuit and oversized scarf—added to the vibrant atmosphere. The Blumarine collection exuded pure joy, playfulness, and whimsy, punctuated by furry statement heels that instantly became must-share recommendations for friends planning upcoming weddings.
Recognizing the physical toll of back-to-back shows, a brief pause for a well-earned reward led straight to a local gelateria near the Duomo apartment, enjoying a sweet treat directly from the balcony. That sugar boost provided the necessary energy for the final show of the day: The Attico. Leaning heavily into themes of intimacy and allure, the brand placed sex appeal at the absolute forefront, even seating guests directly on beds to heighten the immersive, bedroom-like atmosphere.
The day concluded with what easily contended for the title of the best dinner experience in Milan: a late evening at Da Giacomo, where the exceptional food and vibrant room energy were nothing short of immaculate.
Saturday, September 26: Ferragamo Craftsmanship and Culinary Surprises
During the relentless pace of fashion month, weekends offer no respite. Saturday morning began bright and early backstage at Ferragamo in partnership with 111Skin, followed immediately by taking a seat for the runway presentation. The Ferragamo collection stood out for its remarkable material versatility, seamlessly transitioning between supple leather, modern latex, sheer fabrics, and dazzling sequins, all pulled together by exceptional accessories.
Following the Ferragamo show, a quick visit to the Dsquared2 showroom brought a delightful surprise encounter with Britiny. Seeking to properly experience local culinary culture, an impromptu lunch stop at Casa Fiori Chiari yielded what turned out to be some of the absolute best pizza and pasta experienced throughout the entire trip.
With satisfied appetites, the afternoon was dedicated to exploring the historic streets of Milan and handling remote work commitments while the New York office was awake. The evening wrapped up with a sophisticated dinner at Da Niko inside the Bulgari Hotel, where fragrant peppermint tea was served from exceptionally crafted Bulgari homeware.
Sunday, September 27: Final Highlights and Spa Recovery
Sunday marked the culmination of the week, centering on highly anticipated close-up encounters with both Gucci and Ferragamo. Neither house disappointed. At Gucci, the footwear offerings—particularly a striking pair of red shoes—instantly claimed a top spot on the must-have shopping list for the upcoming year. Meanwhile, at Ferragamo, the satin east-west hug bags proved entirely captivating, reflecting exceptional creative direction across the board.
After a final day filled with comprehensive re-sees and bustling conversations, the physical strain of a week spent navigating cobblestone streets in high heels called for serious recovery. A visit to the Irene Forte Spa at the Carlton Hotel provided one of the most deeply relaxing massages of the season. Featuring calming, beautifully scented body oils and specialized attention for tired feet, the spa treatment offered the ultimate restorative finale to a whirlwind week in Milan before packing bags for the next leg of fashion month in Paris.
