It would be inaccurate to say that Milan is as sexy as Venice, as charming as Florence, or as jaw-droppingly gorgeous as Rome. But thankfully the cultural reputation of Italy’s industrial center is on the rise. Over the last three years, the city has done a 180 in the image department, thanks in part to the hoopla surrounding the World Expo (which is still on through October 31). An unexpectedly cool street culture now bubbles along the Brera and Zona Tortona districts. New shops and restaurants have popped up wherever you look, and a fresh band of young creatives has suddenly materialized, armed with entrepreneurial attitudes and robust Instagram accounts.

All of this makes Milan a much more pleasant place to live and a draw for visitors who once bypassed the city for Italy’s more playful and photogenic pastures. That said, Milan remains the epicenter of Italy’s serious business dealings and deeply loyal to its classical roots. This is what makes the city and its hidden treasures so tantalizing. When you come to Milan, you still witness men in great-looking suits riding old-fashioned bicycles to work. You find older gentlemen, dressed to the nines, taking their aperitivo together in sidewalk cafés and lingering for hours over a single Aperol spritz. In the winter, troops of little old ladies are out running errands wrapped in fur coats, wearing panty hose with low-heeled pumps, hair done. No one is in exercise clothes. Manners still count a great deal. And traditions are held on to, despite the push to modernize.

Ask anyone who lives here and they will say everything is hidden in Milan and that it takes years to peel back the layers. This is true to some extent. If you are dropped down into the center of town without a clue as to what to do, the city will not beguile on looks alone. Milan’s most beautiful settings are often revealed behind closed doors, in private homes. Its best moments happen in personal conversation with the city’s inhabitants.

Still, there is plenty to ogle without an insider’s calling card. Though it had a strong run in the fifteenth century, Milan’s golden age was actually after World War II, when groups of talented architects, designers, and artisans came together in shared vision and set the course for the modern design world. The effects of this big bang are everywhere you look. The se- lection of rationalist architecture is superb (the courthouse and the train station are stellar examples), while the prolific output of midcentury designers has populated the city with skyscrapers and churches by Gio Ponti and residences by design god Piero Portaluppi.

New architecture can be found in the city’s recently devel- oped Porta Nuova district, a decade-long urban renewal project that has yielded twenty new skyscrapers as well as parks and retail shops. Smaller, but even more impactful, is the recent arrival of the Prada Foundation, a contemporary arts hub designed by Rem Koolhaas. Set in Porta Romana, it has lit up the city with buzzy relevance.

Design remains at the heart of Milan—there are more ar- chitects living here than plumbers—and it all comes to life in April during the city’s incandescent furniture fair, the Salone del Mobile. Just as crucial, though less welcoming to outsiders, is fashion week. Four times a year the international fashion flock descends on the capital to see what new splendors the leading ateliers have dreamed up. The center of the city is jam-packed with every luxury brand on the planet, but the mood is changing from one of expected commerciality to one of quality, intrigue, and newly discovered talent.

Even the Milanese, who are notorious for complaining about their hometown, concede that Milan is having a moment. Their tradition of abandoning the city every weekend for the chicer shores of Portofino or cooler air of St. Moritz (both of which are a mere two-hour drive) still happens, but not with nearly as much haste.

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Design Those more interested in Art Deco design than the latest suits in the Valentino window should head over to this cozily curated furniture and home-decor outpost in the heart of Brera that also functions as an art gallery. The interiors are a little zany, eccentric, and overstuffed, but this happens to be the city’s preeminent stop for Art Deco furniture.
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Special Only the elegance of the nearby La Scala theater could rival this super sophisticated space that the Milanese call a barbershop. All products, from shampoos to shaving creams, are made in house and specially selected for every customer. Clean-shaven men will wish they had a beard so they could experience the old-fashioned hot shave exactly as it was one hundred years ago.
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It may be slightly off the map, but Carlo Cracco’s sawmill turned restaurant is well worth the trip. Arrive before your reservation to take a cocktail (some of the best in town) at the dedicated bar, but pace yourself for the excellent food to follow, including the salt cod omelet or spaghetti with anchovies.
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Nightlife The roots of this gorgeous pasticceria lie in Milan’s famous La Scala theater—it was the place for the opera and ballet crowd to go after hours to discuss the latest aria. Today it’s a go-to spot for the fashion flock and those who want a taste of Milanese café culture. In addition to the piles of fluffy, buttery pastries, they serve a mean, quick lunch perfectly washed down with a glass of prosecco.
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Shops Housed in the nineteenth-century Palazzo Cagnola and designed by local architectural god Vincenzo de Cotiis, this fashion superstore is the city’s most celebrated multibrand shop. It’s a retail institution that combines the art of design with the art of shopping. Find Milan’s favorite Italian and international labels displayed among exposed walls, floor-to-ceiling glass windows, and marble and bronze accents.
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Cafés Head over to this sweet spot just off Parco Sempione for a good read and a good glass of wine. Part bookshop, part café, this thoroughly modern space (there is even free Wi-Fi—a rarity!) is the perfect meeting place for a frothy morning cappuccino or an early-evening cocktail.
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Hotels Mix the decor of an old boys’ club with the comfort of your dream bed coupled with the charm and humor of a British pub and you have the Yard---a small but distinctive boutique hotel just north of Milan’s Naviglio. The menu at the Doping Club cocktail bar is a gin-lover’s dream.
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