What to Eat, See, Drink, and Buy in Milan, Italy

Including the best negroni sbagliato, still served in whopping handmade glasses.

During my most recent trip to Milan, in June, I bumped into a local I know who asked, at least half seriously, “You’re here so much, why don’t you just get an apartment?” It’s a good question. I’ve been in Milan more than a hundred times since starting as a fashion writer in the ’90s. This year I’ve been four times, and I’ll be back in a couple weeks. I have always loved it.

Milan is a bustling, working city that is home to roughly 1.5 million people. In the past decade, it has transformed into a thoroughly modern place that lives proudly on its reputation for being a world leader in contemporary style, art, and design. And while big-designer fashion is usually a magnet for most visitors, I tend to frequent stores you’ll find only in Milan. And I prefer bars and restaurants that are reliable rather than fashionable. Here’s my slice of Milan.


Trattoria Milanese

Shhh, don’t tell anyone about this spot. It’s at the heart of the Cinque Vie district—literally five narrow streets that represent the oldest surviving bit of medieval Milan. There’s nothing trendy about this classic old-school Lombardian eatery, but the food is great—have the tortellini al sugo d’arrosto (tortellini with beef jus).

Torre di Pisa

What’s the best food in Milan? Undoubtedly Lombardian. But for something more Tuscan, go to the Torre di Pisa. The pro moves are the formidable Fiorentina steak and the heaven-on-a-plate rigatoni alla Toscana with a beef ragù.

A Santa Lucia

A bustling yet comfortable restaurant close to the Duomo with a no-nonsense menu, overlooked by the photos of 400 Italian celebrities who have dined there. Service is attentive, and the food is really, really good. Most of the customers are locals, plus a smattering of fashionistas and a few foreigners in the know.

La Latteria

Determined to do everything their own way from the beginning, husband and wife Arturo and Maria Maggi, the owners since 1965 of the Latteria di San Marco, a former creamery, don’t take reservations, don’t take credit cards, and don’t produce a menu, either. Instead, if you can get a seat, you’ll choose from an ever-changing—and very short—selection of dishes based on the produce dug up that morning from a market garden just outside the city. This is humble Italian food at its very best, and it’s served to just eight tables. The interior is decorated with dated furniture and art of frankly questionable quality. You feel you’ve been invited into a Milanese grandmother’s home for lunch. In a sense, you have.

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Bar Jamaica

Blissfully untainted by the hand or eye of an interior designer, the century-old Bar Jamaica is in the heart of the chic Brera district. It was for decades a popular meeting place for the Milanese luminaries of art, journalism, and photography. Upstairs, a tiny bistro serves basic eats into the night. It may not be the creative hub it once was, but it’s still a great spot for a sharp shot of Milanese espresso or an aperitivo.

Bar Basso

A favorite gathering site of the international design set during the Salone del Mobile, Bar Basso is famed for its negronis. The negroni sbagliato was invented here when a barman replaced the gin in a negroni with a sploosh of prosecco. These—and the regular kind—are served in whopping handmade glasses in two rooms left unmodernized since the 1940s.

Elita Bar

A top choice for downing an early-evening gin and tonic, Elita Bar is in the trendy Navigli district, in the southwest of Milan—a place that is heaving with bars, restaurants, and fashion stores. The small plates are excellent, especially the alici, fried whole anchovies. On the last Sunday of every month, a large antiques market is held along the banks of the nearby Naviglio Grande.


N’ombra de Vin

This is a storied wine bar with a usually crammed sidewalk area that is a magnet for local fashion types—chatting, drinking, and smoking. The cavernous wine cellar downstairs is generally much quieter, but even that fills up at peak times. Great for wine or cocktails and excellent fresh snacks of bread, cheese, and salami.


Amidst all the big-brand designer boutiques on Via Monte Napoleone, Milan’s most famous fashion street, an exciting new arrival is Sease, the performance-wear brand set up by brothers Franco and Giacomo Loro Piana that fuses high-tech functional design and old-school fabrics. Inspired by surfing, sailing, and skiing, the label takes performance sportswear and kicks it up a notch or three. A current collab with maverick environmental-campaign group Sea Shepherd offers pieces made from recycled plastic gathered from the oceans.


Alessandro Squarzi’s sportswear brand is growing fast and available online, but there’s nothing better than buying at the source. Fortela is casual clothing inspired by military and American style and given an Italian edge. There’s a sense of continuity in each new collection, so that something you buy now will likely still look great in ten years, if not better.


Eral 55

For serious vintage hounds, Eral 55 is the essential stop in Milan. It’s a place where you can find secondhand English or American shoes, Japanese denim, and vintage clothing from an expertly curated range of well-known and lesser-known brands. Alternatively, pick from founder Ermanno Lazzarin’s own branded and reasonably priced ready-to-wear clothes or his high-end bespoke label Sartoria Lazzarin, with pieces made directly above the shop.

Massimo Alba

Alba is a veteran at producing luxurious, interesting clothes, many of which he hand-finishes with dyes to add depth. He is a champion of and passionate believer in slow fashion, and his mens- and womenswear is the sort of clothing that you put on once and feel as if you’ve owned it—and loved it—for years. A current hot ready-to-wear buy is the fine needlecord “Sloop” suit he created for Daniel Craig for the opening sequence of No Time to Die.


In men’s style, Italy has a monopoly on modern sportswear with a technical/military bent. Founded by streetwear’s earliest guru, Alberto Aspesi, this brand has been around since the late ’60s but has never looked more relevant. Now designed by a onetime protégé of Aspesi, American designer Lawrence Steele, the label is undergoing a subtle change while remaining true to the original philosophy of wearable functional clothing that is more focused on authenticity than trends.


Fondazione Prada

This multiuse gallery located in a century-old distillery to display and promote contemporary art is one of the city’s biggest recent developments. It also has a Wes Anderson–designed café bar inspired by midcentury Milan cafés.

Museo del Novecento

The novecento, or 900, is how Italians refer to the 20th century. Housed in the Palazzo dell’Arengario, the museum was opened in 2010 to showcase the explosion of Italian modernist art during the 20th century.

Pinacoteca di Brera

One of the more old-school museums of Milan and a pleasant way to while away an afternoon surrounded by some Renaissance greats, followed by an aperitivo round the corner at Bar Jamaica.

Triennale Milano

Named after the Milan Triennial, an exhibition of art and design that ran from 1933 to 1996 and again in 2016, this modern museum devoted to art, design, and architecture features a permanent collection of Italian industrial design, from the Fiat 500 to the Olivetti typewriter.

FromEsquire US

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About The Author
Nick Sullivan
Nick Sullivan is Creative Director at Esquire, where he served as Fashion Director from 2004 until 2019. Prior to that, he relocated from London with his young family to Boerum Hill, Brooklyn. He has styled and art directed countless fashion and cover stories for both Esquire and Big Black Book (which he helped found in 2006) in exotic, uncomfortable, and occasionally unfeasibly cold locations. He also writes extensively about men's style, accessories, and watches. He describes his style as elegantly disheveled.
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