The Italian city of commerce used to be just that. As recently as five years ago, Milan was dismissed by many as the “ugly city,” where lawyers and bankers labored inside gray office complexes and workers toiled away in drab factories.

The city lacked the history of Florence, the beauty of Rome, the views of Amalfi, and the food of Parma. Add to all this the weather element—situated in what is basically a swamp in northwestern Italy, the often cloudy Milan plays host to sweltering summers and frigid, humid winters that seep deep inside your bones—and you have an altogether unwelcoming place.

The entrance to the Milan Expo, 2015.

If you’d asked anyone, even a resident of Milan—especially a resident of Milan—whether they thought the city would ever change, their response would very likely have been an emphatic No! But change, from bars and restaurants to art and culture to internationals of all kinds putting down roots, is happening in Milan. And the rest of the world is taking note.

From A to B and Back Again

Milan wasn’t always as gray as its recent history would suggest. The 80s were a time of hedonism, the golden days of “Milano da bere” (“Milan to drink,” a slogan taking its name from a Ramazzotti-aperitif advertising poster), with Keith Haring swooping in to design the Elio Fiorucci store. “It was easy money, constant partying, and one out of two people in the street was a foreigner,” says the Milanese journalist Renata Molho.

In 1979, Milan Fashion Week overtook Paris’s in terms of profit and volume, and with that came an influx of creatives. Gianni Versace and Giorgio Armani rose to become fashion’s new visionaries. Helmut Newton and Richard Avedon hung out in bars in the city’s up-and-coming Navigli district. In 1988, Franca Sozzani was announced as Italian Vogue’ s new editor, and her brilliant, controversial covers threw the magazine onto the world stage.

But the end of the 90s brought with them the harsh aftereffects of excess. By 2000, around the time Armani opened the Emporio Armani Ristorante & Caffè, the Milano da bere era had dissipated. Milan became the stop on the Fashion Week tour that had journalists grumbling, “Can we just get to Paris already?” The culture of fashion never went away, but the city lost its energy.

Meanwhile, daily life for residents carried on. It was a quiet, sophisticated existence among cobblestoned streets, and a discreet, close-knit local community made it notoriously difficult for expats to break in. “Back in the 2000s, it was the Ice Age,” says J. J. Martin, the American designer behind the brand La DoubleJ, who moved to Milan in 2001 from New York. “It was hard to make friends.”

The city’s attitude toward work is one thing that never changed. As Italy’s economic hub, it has always been ambitious and efficient. People leave their houses in a hurry, in suits and polished shoes. Years ago, Letizia Moratti, the city’s mayor at the time, told me, “Milan is more like New York than you think.”

This fall, Fashion Week—including Roberto Cavalli’s spring-summer 2022 show—was back in force.

But attractions, such as nightlife, were lacking. After long workweeks, most Milanese residents would leave on Friday nights, departing to family homes in the countryside, the Ligurian seaside (home to ritzy Portofino), or the Alps (Cortina d’Ampezzo, Courmayeur, and Saint-Moritz are all a short drive away). Milan on weekends was a ghost town.

Culture was lacking, too. Apart from the discreet Cenacolo Vinciano, which houses Leonardo’s Last Supper, museums were as scarce as sunny days in the city. Fashion Weeks happened for just a few days in the fall and the spring, and Milan’s other draw—Design Week—was just a yearly occurrence. “In between Fashion Weeks and Design Weeks the city felt deserted,” Martin says.

“Back in the 2000s, Milan was the Ice Age.”

But the 2015 Expo, a brash, braggadocio-filled international exhibition that takes place every five years, breathed new life into the city, paving the way for what feels like the 80s redux. Immigrants from Southern Italy started flooding in at unprecedented rates, bringing innovation and upheaval. Over the last five years, the city’s G.D.P. doubled compared to the rest of the country, and, slowly, new businesses have started to open.

“The ‘Milanese’ don’t exist anymore,” says Matteo Dialuce, a Milan-based financial consultant. “Milan is made up of the professionals who have come here because there are opportunities that don’t exist back home.”

After the expo, the annual number of visitors to Milan soared from six million to more than nine million.

The opening of the Fondazione Prada museum in 2015, meanwhile, put Milan on the art-world map. The industrial building’s permanent collection includes works by Damien Hirst, John Baldessari, and Walther de Maria. The same year, MUDEC—Museo delle Culture di Milano—opened its doors.

And next spring, the Pirelli HangarBicocca gallery will host a monumental Steve McQueen exhibition, in collaboration with Tate Modern.

The budding skyline of Porta Nuova, the city’s new fashion quarter.

The city’s skyline has followed suit. Gated communities and luxury condominiums designed by Zaha Hadid, Daniel Libeskind, and the Japanese architect Arata Isozaki have sprung up in the CityLife district, a cluster of high-rise buildings that are home to thousands, including the influencer Chiara Ferragni and her husband, the Italian rapper Fedez, who count nearly 40 million social-media followers between them. (The couple will soon host a reality-TV show on Amazon Prime.)

On the other side of town, in Porta Nuova, a newly minted fashion quarter sits in the midst of high-rises—and their windows spell the names of American brands (Tesla and Nike among them). Last month, F.A.O. Schwarz’s first location in Continental Europe replaced a dilapidated department store in the centrally located Piazza Cordusio. There’s even a Starbucks Reserve Roastery across the street (formerly sacrilege for Italians).

The straightjacketed work culture and the ripe fashion, design, and architecture scenes are making Milan popular among the international expat crowd. And never more so than post-Brexit, which has made London a no-go for many. To say nothing of Paris, daunting mainly because of its residents’ notorious antipathie to foreigners, not to mention the city’s strict residency requirements, including proof of at least a three-year marriage and French proficiency.

Which leaves Milan.

A tax break for the ultra-wealthy, and another for young Italians returning from abroad, help. The now acclaimed M.B.A. program in English at Bocconi University is attracting students who would otherwise have opted to study in the U.K. or the U.S. for college.

“Milan is glamorous,” Jaime de Garcillan, who oversees strategic marketing at the Italian jeweler Pomellato, says. “And younger generations are naturally attracted to art, design, and fashion. It’s a stone’s throw from lakes [including Como], mountains, and the Mediterranean. And of course, who doesn’t love Italy?”

The change is palpable. In just the past few months, I have met Jordanians, Chinese, Swiss, English, and Chileans who have moved to Milan. Foreign faces and accents have become common on the street—a first for the city. “I’ve never had so many clients,” Simone Doti, the owner of training-and-wellness company Cyrovis, tells me.

Milan’s hidden secret: Leonardo da Vinci’s Last Supper, housed in the nondescript Cenacolo Vinciano.

During the cutting-edge design festival Salone del Mobile this year, traffic jams took over the streets. Foreigners bounced between art exhibitions by Maurizio Cattelan, Paul Smith, and Mario Testino. MiArt, a modern-and-contemporary-art fair which went on the following week, is also gaining momentum.

Not one to pass up an opportunity, Natasha Slater, a Brit who has worked in P.R. in Milan for 18 years, started Dinner Conversations, a platform for Milan-based people to meet one other. “The hardest thing about Milan is that there are insiders and outsiders who never mix,” she says. “I feel like everyone wants to change that. I wouldn’t have dreamt this could be possible when I arrived.”

Members’ clubs that the Milan of five years ago would never have dreamt of hosting—Soho House, Spring Place, Casa Cipriani—all have openings scheduled for 2022. The Peruvian-style restaurant chain Pacifico is also opening a private club, which extends across three floors of a formerly abandoned building in the city’s nascent Chinatown. And foreigners can always be spotted at LuBar, a high-end restaurant inside Milan’s Galleria d’Arte Moderna, sipping mezcal cocktails and Sicilian wines.

Ramen and Indian restaurants have opened their doors, too, and traditional panini shops are being replaced with stores selling poke bowls and matcha. When I called Nobu last week for a usually quiet Sunday-night dinner, there wasn’t any space. “Try again on Wednesday,” they told me.

Giorgio Armani once said, “I always dreamt that Milan by night could resemble Milan by day: alive, dynamic, brilliant, and optimistic.” Today that dream feels like a reality.

At the Latteria di San Marco—a local favorite among the fashion crowd—Maria, the owner, made her feelings about my imminent return to New York known. “Why are you going there?!” she said. “All the New Yorkers are here now!”

Elena Clavarino is an Associate Editor for Air Mail