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.

Who What Wear Travels tip: Milan is best enjoyed away from the summer months when many of the shops and businesses are closed for the Ferragosto holiday. Dusci suggests avoiding trips during July and August.

"A little old school" is how Martin describe the Grand Hotel et de Milan, but both she and Dusci effuse their love for the historic gem. "There are definitely some dusty corners, but there's just something stuck in time about this hotel, which I appreciate. It actually has one of the most beautiful restaurants in all of Milan hidden inside. It's like you're in a duke's library," Martin says.

Where to Dine in Milan

"Da Giacomo is my personal favorite," Dusci shares. "I absolutely love their spaghetti with clams. Oh, and you must try their famous Bomba di Giacomo."

Who What Wear Travels tip: Trust your server, insists Martin: "Most Italian waitstaff are truly invested in you enjoying your meal and will give you their honest opinion about the best items and specials on the menu."

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

The fine dining destination near the Duomo di Milano is a pillar of traditional Italian dining and, although its roots are Roman, feels right at home in the northern capital.

Who What Wear Travels tip: While classic institutions offer a quintessential Milanese dining experience, Dusci warns not to limit yourself to just the popular and well-known restaurants. "In Italy, especially in Milan, small traditional trattorias often serve the best food," she says.

Classic Aperitivo Bars in Milan

"The classic, gritty design haunt," describes Martin. "Still caught in the 1960s, this has a kind of slummy Milan vibe but in the best way possible. Go for the Negroni sbagliato that arrives in a goblet the size of a small child. There are always cool people hanging out there."

As one of the oldest sandwich bars in Milan, Bar Quadronno is an institution known not only for its famed panino with salami, ham, and cheese but also its lacquered wooden bar that make it quintessentially Milan. Come for a bite to eat, but stay for a classic aperitivo.

Who What Wear Travels tip: Take an evening stroll after your aperitivo. Martin notes that the Italian ritual of taking a passeggiata, or a stroll around 7 p.m., every evening has become a favorite pastime to bump into friends and neighbors and take a break from the workday. "It's a beautiful lesson in being present," she says.

Newcomer Minerale is where you'll want to head to experience artisanal and natural wine in the heart of the Corso Genova district. The modernist space draws the city's most in-the-know crowd, so you're sure to have plenty of good people-watching too.

The Best Pasticcerias in Milan

There's something transportive about a stop at Marchesi 1824, whether you're in Milan or London or elsewhere. One of the oldest and most renowned pastry shops in Milan, the elegantly designed space makes it a landmark in its own right. You can stop in for a maritozzo or a box of its very giftable cookies or simply admire the towering cakes in the window display.

Who What Wear Travels tip: "Always drink your coffee at the bar," Dusci insists. "This is a true Italian experience you don't want to miss."

Martin isn't shy about her favoritism toward Pasticceria Cucchi. "At La DoubleJ, we've done product collaborations and takeovers with Cucchi twice here in Milan where we totally redid the café," she says. "I know the original owners that opened the space in 1966. It's now under new management, which actually means you can get your cappuccino within the hour now! I love it for aperitivo as well as for a coffee, but they now do a very decent lunch as well."

Dusci shared a number of her favorite spots for Italian pastries, including the famed Sant Ambroeus, which, she says, really captures the authentic Milanese vibe. "Plus, the food and coffee are absolutely delicious—truly yummy treats that make every visit special," she adds.

Where to Shop in Milan

A spot that Dusci highly recommends for shopping in Milan is Cavalli e Nastri. "They offer an amazing vintage selection," she says, adding that her finds from the boutique include such incredible pieces as a Saint Laurent Rive Gauche shearling coat and a Japanese shantung silk kimono. "It's one of the more put-together vintage stores in the city," Martin confirms.

It doesn't get any more iconic than the city's landmark shopping destination at 10 Corso Como. Now with locations in Seoul, Paris, New York, and Doha, the original Milan address houses a meticulous curation of sought-after designer items, skincare, art, food, and so much more.

"Mazzolari Capelli is a real Milanese institution for hair accessories, from headbands and clips to brushes—everything you need for haircare," Dusci shares.

Who What Wear Travels tip: Don't miss the vintage markets, a perfect spot to find unique treasures, held every third Sunday of the month in Brera and the last Sunday of the month along the Navigli, Dusci insists.

What to See in Milan

For fashion people, no trip to Milan is complete without a pilgrimage to the Prada Foundation, the art foundation dedicated to contemporary art and culture that Miuccia Prada and and her husband Patrizio Bertelli have cochaired since 1995. Spend a day wandering the galleries and then enjoy an aperitivo or slice of princess cake at the Wes Anderson–designed Bar Luce attached to the space.

"Though often seen and revisited, Villa Necchi never loses its quiet elegance. It continues to feel timeless and effortlessly inspiring," Dusci notes.

If you look for it, Milan is a visually rich city filled with beautiful details that reference its past. To fully admire its architecture, Dusci says to head to the Stazione Centrale for incredible art deco features.

Who What Wear Travels tip: Do a church hop. Martin says popping into one of the many baroque churches peppered throughout the city is a favorite way to view Milan's beauty. "I've stumbled upon so many beautiful mosaic ceilings, tiled floors, spectacular stained-glass windows, all by accident," she notes.

"Robertaebasta Gallery is one of those rare places where charm and excess coexist beautifully," says Dusci. "Every piece tells a story, and none of them whisper. Incredible curation."

What to Pack for Milan

When packing for Milan, channel your inner sciura. It's a colloquial term the Milanese use in reference to the city's many glamorous and impeccably well-dressed older women—just peek at the account @sciuraglam to see what we mean. Prada should always be a packing reference, naturally, but also the unofficial uniform of Prada herself: a simple knit sweater, a full skirt, and pretty pumps. It's a walking city, but not as much as its neighboring capitals, meaning you can get away with a little bit of a heel. To dress the part of a local, you'll certainly want to.

The number one rule for Milan dressing is to, well, dress up. "Don't wear sweatpants out of the house or workout gear to the office," warns Martin. "While Milan has certainly become a little more gentrified over the past decade, it still hasn't fallen into the West Coast 'athleisure all day' trend." Leaning put-together, elegant, and chic is the move. Of course, that mood extends even to the airport, where you'll be greeted with the world's most stylish travelers the moment you touch down at Malpensa, and nothing makes as chic a statement as arriving with a Rimowa Rollaboard in tow.