Models present creations from the Giorgio Armani Spring/Summer 2026 collection during Fashion Week in Milan, Italy, on Sept. 28, 2025.Claudia Greco/Reuters
Milan is Italy’s undisputed playground for the well-heeled – a city of swank hotels, 17 Michelin-starred restaurants and posh lounges scattered across nine distinct zonas (neighborhoods). Fashion Week draws its usual parade of big names, but Milan’s cool has never been solely in the possession of headline designers and front-row celebrities. It’s shaped, season after season, by the working-class insiders who keep the machine humming.
These are not the movers and shakers but the makers: the people who produce, adjust, record or assess runway looks. Stylists sprint between appointments, hunting vintage treasures on elusive consignment racks. Patternmakers duck into tiny cafes for quick espressos before all-night sessions. PR professionals stretch the Milanese aperitivo into strategy sessions, deals sealed over small plates and spritzes.
For more than 20 years, stylist Dinalva Barros has been a constant at Milan Fashion Week, styling editorials for publications such as Vanity Fair, Vogue Italia, Glamour and Marie Claire Italia. Last season alone, she styled 16 catwalks. During her downtime, she turns to her mental black book of where insiders dine, sip, shop and quietly do business between shows.
Front-row buyers and celebrities tend to stay central, gravitating toward the Ferragamo-owned Portrait Milano hotel, home to the roaring 1920s-tinged Rumore Bar. Soft cheetah-print stools and Red Hook cocktails are part of the draw. Access comes at a price – often upward of €60 ($97) a drink (likely priced for generous expense accounts) – and reservations are essential (the website notes a 90-minute seating limit). The bar’s clientele reflects the Italian label’s polish. “Some of the chicest, most luxury-driven people in the world are there,” Barros said. “It’s worth stopping by just to look at their handbags.”
Other ready-to-wear buyers make a beeline for the bar at The Plein Hotel, as well as its Japanese fusion restaurant, Sukaru Ba. Bricked in gold skulls and glossy black stone, the space mirrors the opulent, baroque sensibility of German fashion designer Philipp Plein. The cocktail menu reads like a mood board: Matcha Fizz made with Kyoto-based tea gin, Saigroni featuring pho-infused vodka and Campari.
The only comparable perch for international fashion folk is the rooftop at Terrazza Gallia atop the Excelsior Hotel Gallia. The wine list spans Italy from north to south, but it’s the skyline view – anchored by UniCredit Tower and Torre Gioia 22 – that draws guests in.
When the night calls for something sweeter, insiders head to Café Parigi at the Palazzo Parigi Hotel. Post-dinner, a good move is a glass of Ben Ryé Passito di Pantelleria from family-run Sicilian vineyard Donnafugata.
Five top trends from the fall/winter runways at New York Fashion Week
A more local rhythm can be found beyond the hotel circuit. At Bar Basso, a Fashion Week institution, light wood and blush-pink panels glow beneath crystal chandeliers. The cocktail list, titled “The Drinkers,” features 24 pours named for cultural figures who once gathered there. “It’s where many go after the shows,” Barros said, adding that the people-watching rivals the runway.
The stylist’s favourite spots, however, are located outside of the city centre in Porta Venezia, known for its LGBTQ nightlife, reasonably priced retail and low-key energy.
Off duty, she can be found nursing a Negroni at Eppol, where tables set for aperitivo fill with charcuterie plates, tagliatelle with porcini and baked pumpkin. Here, PR teams, makeup artists and interns compare notes on shoots won and lost. “The seating outside – even in winter with heat lamps – is perfect for someone like me who is always looking at street style,” she said. “People here mix high fashion with pieces from their parents’ or grandparents’ closets.”
A short walk away are two of the city’s best vintage haunts. BIVIO stocks womenswear and menswear from labels such as Comme des Garçons, Roberto Cavalli and Valentino, while Frab’s Magazines draws editors and art directors with hundreds of fashion and culture titles from around the globe. Owner Anna Frabotta, a professor at the Institute of European Design in Milan, announces new arrivals weekly via Instagram. Frab’s is proof that print is enjoying a renaissance in Italy, with culty design magazines such as More Than Cat Food, Mother Tongue and Delayed Gratification flying off shelves.
Fashion photographer Lucia Giacani, whose images often land in Frab’s staples such as L’Officiel and The Collector, splits her time between residential Piazzale Dateo and Porta Venezia. For brunch, she’s a fan of the Michelin-star bakery hotspot Pan, where she has a choice of items such as the Shoku-toast (made with prosciutto cotto and Comté Marcel Petite) or a brunch plate with salmon, a soft-boiled egg, labneh and cabbage.
For dinner, Giacani keeps things traditional at Onest, a small Milanese eatery with a reasonably-priced seasonal menu. “I usually order whatever the chef or server suggests and it never goes wrong,” Giacani said.
Closer to the Dateo railway stop, Fashion Week drivers grab a quick €12-lunch between pickups at Amo Pizza. It includes pasta, a meat dish, a veggie side and a glass of house red.
For fashion filmmaker and content creator Sarah Sophia Franco, who works with houses such as Armani and Stéphane Rolland, mornings start at Hygge near central Milan. The Italian-style French toast – heavier on egg yolk than its North American cousin – delivers the stamina she needs for long days on set.
If she’s in a rush, she grabs a cream puff and shakerato at Pasticceria Biffi, a legendary pastry shop that opened in 1847. Influencers tap at laptops, edit reels and post their takes on the latest collections. You’ll catch the same type of crowd over at Bar Luce on Milan’s south side, a Formica-clad café that serves a pricier espresso, likely because it’s attached to the Rem Koolhaas-designed Fondazione Prada, which houses works by artists such as Damien Hirst and Louise Bourgeois.
Amidst the chaos of Fashion Week, one thing is clear: in Milan, style isn’t confined to one postal code, type of person or bank balance.