The glut of cranes and mid-development high rises on the 50-minute drive south from Malpensa Airport — one of Milan’s three international airports — into the city centre is testament to its rapid transformation. The buzz on the streets is both par for the course and fuelled by Milan Fashion Week, the reason for our presence there. I am accompanying South African fashion designer Wanda Lephoto on his maiden showcase in a city that loves art and architecture but is utterly seduced by fashion.
Based mainly in the city centre, we will explore what we can in a short period of time, as we already know we owe ourselves another trip. All clichés observed, Milan will make you fall in love with dressing up again. As our driver drops us off unceremoniously some metres from our hotel, every square metre of pavement around us is one sight of rampant sprezzatura after another. There are well-dressed people everywhere — on foot, on bicycles, and in the frequent Italian mega sportscar. I can imagine the frustration of each beautiful soul sauntering by at having had to stay indoors and dress like an American for two years.
Our abode, the Velvet Grey, a stylish boutique hotel, is located amid all this, but you wouldn’t say so — outside my fourth-floor window the skyline is filled with picture-book Milanese buildings and fairy lights from the restaurant below. Here, we are close to the shopping at Galleria Vittorio Emanuele II and the snaking queues at Duomo di Milano (Italy’s biggest church), and hardly a kilometre from Duomo Square, which is busy pretty much all year round. On our first visit, there is a march for Ukraine.
Hundreds come out, chanting and walking by Valentino, Tod’s, Louis Vuitton, Gucci, Jil Sander, Cartier, and others — the luxury-brand roll call framing this scene is staggering. A short ride on the tram or a leisurely walk south you find yourself in the popular “streetwear” enclave of Corso di Porta Ticinese/Navigli, frequented by a younger crowd and the place for your Carhartt and Stüssy fix. Further southeast, on the outskirts of Porta Romana, you find the famed Fondazione Prada, which is always one exhibition away from blowing your mind.
Later that night, we stand outside the Bottega Veneta show, amid a sea of young fashion fans, phones in the air, expectant. I am told Frank Ocean may be exiting soon. I like Frank Ocean, but I — like a rookie, in my secret socks — am not going to freeze on the streets of Milan to see him. I spot the actor Yahya Abdul-Meteen II leave the show as we learn from history and give up on expecting anything from Ocean until he is well and ready, and look for something much more accessible — food.
I vow to finish the long list of “must-see places” in Milan that we never got close to finishing, top of the list being a grown-up bar
We have to wait for the authentic Italian we crave — nothing decent opens for dinner before 7pm — so we kill time with a drink at Juice Milan X Mama Burger, a meeting space for Gen Z, with trap music and attitude flowing from the bouncer to the waitrons: you may be important as a customer, but the staff is far more vital (and way cooler), one would have to believe. Dinner at Al Cantinone Trattoria — established in 1930 — is a practised, polished but warm affair, with the chianti chosen by one of my dinner mates complementing the veal splendidly.
On another night, I meet a crowd of Saffers and a gracious Italian at Taverna Moriggi — a historic dive bar tastefully renovated and reopened in 2018, serving classic Milanese fare. I arrive late — a South African, a taxi, and an ATM meet in Milan, the joke would begin — having missed out on an aperitivo and live jazz, but there’s just enough time to taste some starters being passed around before I text my wife about the cracking ravioli main.
Our food adventures will wane, wax, and wane after that, and after Lephoto’s show — a well-received smash — we see about a celebratory drink. Tutti Fritti, popular with the Supreme army and famed for a long craft-beer menu, closes after one drink (it’s a Monday, after all) but the barman has a plan. We file into two taxis and head to Dirty Mondays, where the rallying cry is “Live fast, die Dirty”. With an irreverent rock ’n roll theme popping up in this city and Los Angeles, the soundtrack on this night is all manner of tunes in the rock genre, from punk and grunge to more poppy anthems.
The energy is young and frenzied, the floors suitably sticky, and the drinks cheap. As I walk the 15 minutes back to my room, making mental notes about things that cannot be forgotten as we depart the next day, I vow to finish the long list of “must-see places” in Milan that we never got close to finishing, top of the list being a grown-up bar, like the famed Bar Basso. One must also explore the north of the city, in neighbourhoods such as Isola and Pasteur district/Via Padova, where some of the more interesting and multicultural of Milanese reside. I may even take my place in the queue at Duomo, but don’t count on it.
Good to know
Visas: South African passport holders must obtain a Schengen visa to enter Italy.
Covid: Travellers need to fill in the Passenger Locator Form before entering Italy, and show the document to the carrier. They also need to present a Covid-19 vaccination card or a negative molecular or antigen test. Those who do not show this documentation can still enter, but will have to undergo quarantine for five days.
• Siphiwe’s trip to Milan was made possible by Bulldog Gin.
• From the May edition of Wanted, 2022.