Simon Holloway’s Guide to Milan

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The Agnona creative director dishes on his favorite spots in his adopted city.

British-born Simon Holloway may be an Englishman to the bone—his caffeine source of choice is tea, after all—but his eye, these days at least, is nothing if not Italian. As the creative director of the Milan-based luxury fashion brand Agnona since 2015, Holloway's use of refined furs, wools, and leathers on streamlined silhouettes demonstrates a true affinity for that particularly Italian way of blending the traditional with the cutting-edge. But the sensibility, it seems, runs more than skin-deep. Having lived in Milan, where the luxury womenswear brand is based, part-time for the past three years (he still splits his time with London), Holloway has picked up a few favorite spots of his own in the sophisticated city, including where to find the best osso buco, souvenirs, and “cuppa’" in town. Read on for his top places to eat, stay, and explore in the city.

What neighborhood do you live in, and how long have you lived there?

The Magenta District. I live close to the Church of Santa Maria Delle Grazie, where you can see L'Ultima Cena of Leonardo da Vinci. It's quite magical to see early in the morning as dawn is breaking or sensitively lit up at night. I have been there for about a year and the view is never tiring to behold. 

Where would you put up friends visiting town?

The Mandarin Oriental in Milan is truly chic and the service is simply impeccable. It is centrally placed between the city's golden triangle shopping district and the more neighborhood-ish vibe of Brera. (Via Andegari, 9; 39-02/8731-8888; mandarinoriental.com)

Where is the best place to find the city's signature dish?

I love to order osso buco with the delicious risotto Milanese at Bice. It's still one of the classic restaurants of Milan. (Via Borgospesso, 12; 39-02/7600-2572; bicemilano.it)


Courtesy Ceresio

What is your favorite restaurant to take visitors?

The Langosteria Bistro has exceptionally fresh fish and crudo. The preparation is minimal and perfect, and the service is warm and crisp. They also have a beautifully curated wine list. (Via Privata Bobbio, 2; 39-02/5810-7802; langosteria.com)

Where can you find the best cocktails?

The Doping Club at the Yard Hotel has perhaps the most serious—and seriously good—cocktails in Milan. The surroundings are plush and eclectic; the handsome staff are attentive and always seduce you into one round too many. (The Yard Hotel, Piazza Ventiquattro Maggio, 8; 39-02/8941-5901; thedopingclub.com)

Where would you choose to splurge on a night out?

I don't really go out-out. I tend to be a dinner person. Ristorante Da Giacomo for sea bass al sale for two and a fabulous bottle of Vintage Tunina. Maybe it's because I'm British, but I have a total fetish for the dessert trolley there. It's all about the bomba Giacomo, a little slice of heaven consisting of two layers of fine pastry and a wedge of stiff cream studded with those minuscule wild fragole di bosco. Insane. (Via Pasquale Sottocorno, 6; 39-02/7602-3313; giacomoristorante.com)

What is your go-to after-hours bar?

Ceresio 7 is a really fun place to go for dinner. Its late century-inspired interiors are cool, the crowd is always beautiful, and the staff work overtime to ensure you have a great night. (Via Ceresio, 7; 39-02/3103-9221; ceresio7.com)


Courtesy Getty Images

Whats the best way to spend a Saturday afternoon in town?

A trip to the Fondazione Prada. The campus is stimulating, culturally brilliant, and architecturally stunning. And the Cafe is a riot of Italian kitschy cool. (Largo Isarco, 2; 39-02/5666-2611; fondazioneprada.org)

What is your Sunday morning routine in your neighborhood?

On Sundays, it's about trekking back to the Ceresio 7 to work off Milan's gastronomic excesses at its state-of-the-art gym. 

Where is the best brunch?

At Ceresio 7, I go upstairs for brunch and some R&R around their rooftop pool—Milanese style. Although I don't overeat at brunch, there's no fat on display here! If you have time, you can go for a walk at Isola District, where there are many places for a very good brunch. Or at Babitonga Cafè, a new cafe and bookshop inside the Fondazione Feltrinelli. (Viale Pasubio, 5; 39-02/495-8341; fondazionefeltrinelli.it

Where do you go for the perfect cup of coffee?

I don't drink coffee—basically sacrilegious behavior in Milan. I'm a tea drinker through and through. A lovely pot of earl grey at [Pasticceria] Marchesi surrounded by pastel colored sweets and Milanese pasticceria is quite divine. (Galleria Vittorio Emanuele II; 39-02/9418-1710; pasticceriamarchesi.it)


Courtesy Pasticceria Marchesi

Whats your favorite view in town (that tourists might not know about)?

From Terrazza Triennale, you can see Milan from a different viewpoint—while enjoying a great dinner or drinks atop one of the great palaces of Milanese design culture. (Viale Alemagna Emilio, 6; 39-02/3664-4340; osteriaconvista.it)

Whats your favorite path or trail to follow on a walk?

Milan is relatively small—it only takes a short time to walk across town. It is truly marvelous to see the formality of Milanese architecture punctuated with the majestic modernism of Gio Ponti's Pirelli Tower and RAI building.

What are your favorite offbeat cultural attractions?

Have lunch at the Villa Necchi Campiglio and then tour the beautiful house designed by Piero Portalupi, an architectural jewel in Milan. (Via Mozart, 14; 39-02/7634-0121; visitfai.it)

Whats your favorite shop or boutique?

Antonia offers a brilliant shopping experience in Milan. She's an inspiring person and it's reflected in her gorgeous store. Both the men's and women's boutiques have a vibe that's refined, yet you can find everything that's "just right" for the moment. (Via Cusani, 5; 39-02/8699-8340; antonia.it)

Whats the ultimate souvenir from your townsomething you can only get there?

I love these Biellesi biscotti from Pasticceria Jeantet: canestrej and canestrelli. They aren't exactly Milanese, but close enough. I have seen the most strictly dieted fashion people instantly renounce any aversion to gluten and sugar, devouring an entire bowl within minutes. (Piazza Vittorio Veneto, 16; 39/015-21415; jeantet.it)