The Fashion-Insider Guide to Milan: The Most Stylish Places to Stay, Shop, Dine, and Go
Welcome to Who What Wear Travels, a series of curated guides to destinations the fashion set loves. Consider this your download on everything from the chicest stays to the most memorable meals to the perfect travel wardrobe, all vetted by stylish locals and well-traveled fashion folks.
"In a nutshell, Milan is like a very big small town," says J.J. Martin, founder of lifestyle brand La DoubleJ. The Italian fashion capital has long been an endless trove of style inspiration, and while we keep a close eye on what's happening there during Milan Fashion Week each February and September, the city, which normally possesses a cozier quality, is currently rising among the ranks as a European force to pay attention to throughout the rest of the year too.
Now, with an exciting game of musical chairs happening at the major labels, all eyes will be on Milan and what unfolds as new designers—Louise Trotter at Bottega Veneta, Demna at Gucci, and Simone Bellotti at Jil Sander—present their debut spring/summer 2026 collections. Without a shadow of a doubt, Milan is the moment.
Fashion is one thing, but Milan is also a huge design city and home to Salone del Mobile, the annual interior design fair that draws a stylish international crowd to rival that of fashion week. "On top of that," Martin continues, "the city is just swirling in the Italian juiciness of craft and quality and beauty and food and all of the things that make living in Italy just delightful." Of course, what Milan lacks in romance compared to other cities in Italy it gains in elegance and tradition, two things that flourish when it comes to Milanese dining and the unique art deco architecture it's known for.
Silvia Dusci, founder of jewelry label Le Sundial, says that wandering through the narrow historic streets—admiring the beautiful building entrances, gardens, and old doors—is a treasured pastime. "It's a great mix of Italian charm and international energy," she muses. Lately, though, she admits that Milan is earning even more attention and seeing much more growth, making it a perfect moment to spotlight the city and all of its most classic spots.
Where to Stay in Milan
You're just as likely to see the Milanese stopping by for an aperitivo underneath the sweeping porticos of the Portrait Milano as those vacationing, says Kristen Nichols, Who What Wear associate director of special projects, thanks to its prime location and stunning décor. Beloved by locals and visitors alike, the hotel is housed in a former ancient seminary, giving the space a sense of stately significance. The inside, however, tells a different story. It's all sleek, modern furnashings with jewel-toned accents that blend the contemporary with the art deco. It should come as no surprise to learn that it's owned by Italian fashion royalty, the Ferragamo family, and has, therefore, earned a spot as a fashion-person favorite.
Bulgari hotels are the most sought-after stays among the fashion crowd, but none are quite as iconic as the Milan destination, which was, of course, the jewelry house's debut in hospitality. The space is marked by Zimbabwean black marble, teak, and Vicenza stone that give it a quiet grandeur and make it a much-welcomed oasis that, despite being situated adjacent to Milan's main shopping street (Via Monte Napoleone), feels like an exclusive hideaway.
