Via Montenapoleone, 1966. Photograph by Ferdinando Scianna.

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 selection 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 developed 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 architects 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.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Antica Barbieria Colla Via Gerolamo Morone 3
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.

Antonia Via Cusani 5
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.

Biffi Corso Genova 6
Since the 1960s, when the Biffi sisters first opened their boutiques, the most buttoned-up and sartorial Milanese have come here for a highly curated selection of niche Italian labels and a selection of international brands, including Ralph Lauren, Marc Jacobs, and Lanvin.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Carlo e Camilla in Segheria Via Giuseppe Meda 24
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.

Ceresio 7 Via Ceresio 7
Everything about Ceresio 7 screams attention to detail, from the Dimore Studio ― designed restaurant to the rooftop pool with stunning views over the city. It’s not only the perfect perch for a sexy aperitivo, but also a sleek urban retreat when you want to set up shop poolside for the day.

Pasticceria Cova Via Montenapoleone 8
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.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

E. Marinella Via Santa Maria alla Porta 5
Old-school dressing with a hint of English charm is the mood of this Milanese tie mecca that’s been outfitting the city’s signori for the last two generations. Founded in Naples in the early twentieth century, Marinella was famous for its shirts before its loyal customers realized that the sophisticated, impeccably cut ties were the real gems.

The Yard Piazza XXIV Maggio 8
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.

Iliprandi Piazza San Marco 1
Well-heeled, in-the-know Italians head to this shop in the center of Brera to make their shoe selection from a wide range of international brands such as John Lobb, Carmina, and Church’s. The chesterfield leather sofas and armchairs combined with the old-school staff make this an ideal shopping destination for visiting dandies of all stripes.

Giacomo Arengario Via Guglielmo Marconi 1
Milan’s famous Da Giacomo eating empire now encompasses six establishments throughout the city (all of which are worth checking out) but the Arengario, with its stunning views of the Duomo, is one of our favorites. While difficult to secure a table in the glass atrium overlooking the fifteenth-century church, it’s a great spot for a smart business lunch or dinner.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Excelsior Hotel Gallia Piazza Duca D'Aosta 9
Designer Marco Piva has converted the space, originally opened in 1932, into a glitzy megahotel. The Shiseido Spa, which is excellent, offers a range of treatments across two floors.

11 Clubroom Via Alessio di Tocqueville 11
Just off Corso Como, this trendy cocktail bar functions just as well for a post-work drink (although, nota bene, the decor is a bit aggressivo) as it does for a late night out.

Il Salumaio di Montenapoleone Via Santo Spirito 10
The prices are steep, but this elegant dining superspot does not disappoint. It’s great for lunch or a formal dinner, but our favorite is the aperitivo complete with a top salami and cheese spread. Sip a spritz tucked away in a hidden, open-air courtyard that will make you feel like Milanese nobility.

Mandarin Oriental Via Andegari 9
Italian contemporary design meets old-style grandeur in this luxury landmark that occupies four connected eighteenth-century houses around the corner from La Scala. Enjoy southern Italian cuisine at Seta, the in-house restaurant, but be sure to have an alfresco drink beforehand in the hotel’s intimate, gorgeously designed garden. The spa is another not-to-miss spot.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Al Bazar Via Antonio Scarpa 9
It’s easy to see how the handsome and well-aged Italian shop owner Lino Ieluzzi has inspired a generation of younger, sportier dressers to adapt an old-school-goes-cool way of wearing clothes. He’s always in his signature double-breasted jacket that does not come cheap, but at least you’ll leave Milan more stylish than when you arrived.

Borsalino Galleria Vittorio Emanuele
Myth and legend surround this old-style Italian hatmaker that has been handcrafting iconic bowler and straw hats for men and women for more than 150 years. Giuseppe Borsalino’s original designs have lured a laundry list of international celebrities, and his classic Italian style continues to be relevant today.

WP Lavori in Corso Via Borgogna 3
Authenticity and quality are the two pillars of this small shop specializing in casual sportswear for men and women. For the last thirty years, WP has brought international brands (most famously Barbour and Woolrich) to Milan. In fact, it is so ingrained in the fabric of Milan that Rizzoli dedicated an entire book to it.

Pisa Orologeria Via Verri 9
If you manage to make it down Montenapoleone without breaking the bank, pop into Pisa. A selection of top vintage and new watches from heavy hitters Rolex, Patek Philippe, and Jaeger-LeCoultre, as well as newer players Parmigiani and Greubel Forsey, are on display, and a smart sales team is on hand to answer all your horological queries.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Bernardini Luxury Vintage Corso Magenta 68
A rare Patek Philippe watch or customized Louis Vuitton trunk? A set of gold vintage Hermès champagne wands to control the amount of bubbles brimming from your flutes? Milan’s most charming man-about-town Max Bernardini has all this and more. On early evening visits, he will happily bust open his stocked bar to offer an aperitivo or two.

Roberta e Basta Via Marco Formentini 4
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.

Libreria Utopia Via Marsala 2
Pop into this small but jam-packed book boutique to find a careful selection of independent Italian publishing labels with many tomes celebrating the history of Milan itself.

Libreria del Mondo Offeso Via Cesare Cesariano 7
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.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Lorenzi Corso Magenta 1
The Milanese are still mourning the closure of Lorenzi on Montenapoleone, but luckily for us, the sister establishment of the famed cutlery specialist is still operating out of a small shop on Corso Magenta. Come here for the chicest mix of miscellany, including old-school shaving accessories, the odd pepper mill, and oyster shucking gloves.

Preattoni Via Della Spiga
Drugstores in Milan are chic, and Preattoni is no exception. While many of its niche products are available from its online site, treat yourself to a true Italian shopping experience and pop into the tiny shop, where you can find everything from beard oil to bath salts on one of Milan’s poshest streets.

Bar Basso Via Plinio 39
On the fringes of the city center, Bar Basso isn’t fancy, but its Negroni — served in a gigantic glass with a signature snowball-sized ice cube — attracts an ecclectic crowd of locals. This is our top pick for cocktails, and it shouldn’t be missed.

photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Trattoria Arlati Via Alberto Nota 47
This cozy trattoria is a mix of bric-a-brac and taxidermy that happily contrasts with the otherwise ordered and neat design. The food is old-school — pâté and rabbit thighs are served alongside pappardelle with porcini and buttery snails — but it hits the nail on the head of Milanese classics such as risotto Milanese. Tuesday nights are dedicated to jazz, which plays from the raucous wine cellar on the ground floor.

Peck Via Spadari 9
No one has figured out how to transport that kilo of gelato back to New York, but fear not! Those looking to take home some cult Milanese edibles can head over to mega – food hall Peck, where a range of (expensive) delicacies from small handmade chocolates and fluffy panettone to cheeses and salted meats can all be wrapped up to take away. Gourmands not in a rush can enjoy a smart and tasty meal at the restaurant.

Il Bacaro del Sambuco Via Montenapoleone 13
This elegant lunch spot isn’t cheap, but it’s a favorite, semi-hidden spot for those busy shoppers shuffling up and down Montenapoleone. The tortelli di erbette and beef tartare are two dishes not to skip. If you missed lunch, come back at six o’clock for a Negroni and you’ll enjoy the city’s chicest and least obvious aperitivo spot.

Paper Moon Via Bagutta 1
The decor leaves much to be desired, but there’s a reason why this centrally located, bustling restaurant has become a respected favorite for locals and tourists alike. It has been serving up fresh Italian classics like cheese ravioli with porcini and truffle cream for more than forty years. Not so light on the waistline, but well worth it.

photograph by STEFANO TRIULZI

Raw Via Palermo 1
This boutique specializing in tabletop objects in the heart of Brera is Milan’s answer to the wunderkammer. It has a well-balanced mix of vintage and contemporary decorative items that are nearly impossible to resist, whether it be a paperweight, a scented candle, or a small leather good.

Palazzo Parigi Hotel Corso di Porta Nuova 1
Designed by Pierre-Yves Rochon, this former palazzo from the fifteenth century is now a supermodern, sleek (and some say too shiny!) hotel in upmarket Brera. The interiors are inspired by 1930s design, and the location boasts a private garden where you can decide whether to take an early-morning coffee, midafternoon lunch, or drinks.

courtesy of STRAF HOTEL & BAR
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI
photograph by STEFANO TRIULZI

Straf Hotel & Bar Via San Raffaele 3
This boutique hotel is steps from Piazza del Duomo, but its minimalist design (spearheaded by überarchitect Vincenzo de Cotiis) will make you feel miles away from the hustle and bustle. The space is hip, but be prepared for raw and stark materials. Non–hotel guests should check out the downstairs bar, a hotbed of cool cocktails and DJ beats.

Spotti Viale Piave 27
For more than thirty years, Spotti has been selecting and showcasing the latest in interior design as perfect for a home office as for a kitchen or bathroom. Milan-based Studiopepe curates the windows, where you’ll find Italian evergreens such as Cappellini armchairs, B&B Italia sofas, Knoll tables, and Flos lighting.

Spazio Rossana Orlandi Via Matteo Bandello 14–16 Milan’s reigning design queen Rossana Orlandi is the hottest ticket in town during Salone del Mobile, but those in the city during the off-season can still enjoy her eponymous gallery and shop, where you’ll find a range of niche products by Nacho Carbonell and Maarten Baas handpicked by Orlandi. After a spin around the space, enjoy lunch next door at Orlandi’s restaurant, the Paola Navone ― designed Marta.

Society Via Palermo 1
Head over to Society, where you can own the same linens and bedding preferred by the chicest men (and women!) in Milan. Don’t limit yourself to sleep essentials — there’s a supersoft range of bath towels and throw blankets, too. Warning: You may experience sticker shock, but when it comes to comfort, one should never skimp.