The Fashion Insider's Guide to Milan: The Most Chic Locations for Accommodation, Shopping, Dining, and Exploring

      Welcome to Who What Wear Travels, a collection of carefully curated guides highlighting destinations favored by the fashion elite. This serves as your comprehensive resource for everything from stylish accommodations to unforgettable dining experiences to the ideal travel wardrobe, all approved by fashionable locals and seasoned travelers. "In essence, Milan resembles a large small town," states J.J. Martin, founder of the lifestyle brand La DoubleJ. The Italian fashion hub has long been a rich source of style inspiration, and while we closely monitor events during Milan Fashion Week each February and September, the city, which typically has a more intimate feel, is gaining traction as a significant European destination worth noting throughout the year. Currently, with an interesting shuffle of talent happening at major fashion houses, attention will focus on Milan as new designers—Louise Trotter at Bottega Veneta, Demna at Gucci, and Simone Bellotti at Jil Sander—unveil their inaugural spring/summer 2026 collections. There’s no doubt, Milan is the place to be.

      Fashion aside, Milan is also a major design city and hosts Salone del Mobile, the annual interior design fair that attracts a stylish, international audience rivaled only by fashion week. "Additionally," Martin adds, "the city is infused with the Italian richness of craftsmanship, quality, beauty, and food—everything that makes life in Italy a joy." What Milan may lack in romance compared to other Italian cities, it compensates for with elegance and tradition, qualities that shine in Milanese dining and its renowned art deco architecture. Silvia Dusci, founder of the jewelry brand Le Sundial, enjoys wandering through the narrow historic streets, admiring the beautiful entrances, gardens, and ancient doors. "It's a wonderful blend of Italian charm and global energy," she reflects. Recently, she observes that Milan is garnering even more recognition and witnessing significant growth, making it an ideal time to highlight the city and its classic attractions.

      Where to Stay in Milan

      You're just as likely to spot Milanese locals enjoying an aperitivo under the expansive porticos of the Portrait Milano as you are to see tourists, according to Kristen Nichols, Who What Wear's associate director of special projects. This is thanks to its prime location and stunning decor. Cherished by both residents and tourists, the hotel was formerly an ancient seminary, endowing it with a sense of historical significance. Inside, however, it's a different story, featuring sleek, modern furnishings with jewel-toned accents that harmonize contemporary design with art deco influences. Unsurprisingly, it's owned by Italian fashion royalty, the Ferragamo family, and has become a favorite among fashion enthusiasts.

      Bulgari hotels are the top choice for those in the fashion scene, but none are as iconic as the Milan location, which marked the jewelry house's first foray into hospitality. The venue is distinguished by Zimbabwean black marble, teak, and Vicenza stone, providing a quiet grandeur and creating an inviting oasis that, despite its proximity to Milan's main shopping street (Via Monte Napoleone), feels like a secluded retreat.

      Who What Wear Travels tip: Milan is best experienced outside of the summer months when many shops and businesses close for the Ferragosto holiday. Dusci recommends avoiding travel in July and August.

      "When I say ‘a little old school,’ I refer to the Grand Hotel et de Milan," Martin explains, expressing her admiration for this historic treasure. "It may have a few dusty corners, but there's something timeless about this hotel that I appreciate. It even features one of the most beautiful restaurants in Milan hidden inside. It feels like you're in a duke's library," says Martin.

      Where to Dine in Milan

      "Da Giacomo is my absolute favorite," shares Dusci. "I adore their spaghetti with clams, and you simply must try their famous Bomba di Giacomo.”

      Who What Wear Travels tip: Trust your server, Martin insists: "Most Italian waitstaff genuinely want you to enjoy your meal and will honestly recommend the best dishes and specials."

      "This place never gets old," says Martin of Bice. "It's an upscale classic trattoria with great food, and everyone there treats my dog like royalty. The reason I cherish these places is that I know them, and they know me—it's very personal. However, keep in mind that your experience as a tourist might differ."

      This fine dining spot near the Duomo di Milano is a bastion of traditional Italian cuisine, and although its origins are Roman, it feels perfectly suited for the northern capital.

      Who What Wear Travels tip: While classic institutions offer an authentic Milanese dining experience, Dusci cautions against limiting yourself to merely popular and well-known eateries. "In Italy, particularly in Milan, small traditional trattorias often serve the best food," she advises.

      Classic Aperitivo Bars in Milan

      "This bar embodies classic, gritty design," describes Martin. "It's suspended in the 1960s, capturing