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How to Fall in Love with Milan

“The city is best experienced on a slow, aimless stroll. It’s on these wanderings and meanderings that I fell for Milan.”

My first visit was in winter. Cold, drab, grey. All that 1960s and 1970s architecture, tower blocks that reminded me of council estates, functional but undeniably ugly. Smudge brown against grey clouds isn’t exactly the palette of dreams. 

Unlike the Italian cities I had fallen for instantly: Palermo where I lived for six months, Rome (my first love) and Lecce, Milano just wasn’t hitting the spot aesthetically. Not to mention socially. Everyone seems to keep the same friendship group from birth. Impossible to penetrate as an outsider and oh-so cliquey. The family I’d married into, though, was Milanese, so I’d have to either ‘like it, or lump it’, as my British mother would say. 

The industrial heart of Italy, Milan is not one that will effortlessly win you over at first sight, especially if like me, you’re drawn to beautiful things. I’m not the only one to have said it. There’s an online Quora thread debating the reasons behind the city’s ugliness, in which one person who clearly doesn’t mince their words describes Milan as ‘A filthy and smelly city full of pretentious, strutting and self important people. It has no decent architecture other than a ridiculous church surrounded by McDonalds, KFCs, overpriced clothes shops, rip off souvenir stands, pick pockets and rude Japanese tourists.’ OUCH.

Coy with a tough skin, Milan is a city that reveals itself to those that truly want to discover it. Yes, much of its impressive historic architecture was lost to the second world war and in place of it, functional tower blocks were built to serve the masses that moved to the city to work in the boom years. There’s plenty of diamonds to be found in that rough, though. Having returned five times since my first visit and spent at least a week on each of those occasions ‘getting to know’ Milan, the dark horse has won me over.

A chink in my Milan-hating armour first appeared on the Navigli. An interconnected chain of canals that have woven through the city since the Middle Ages, the Navigli are to me, the prettiest part of Milan. Built to transport the vast quantities of marble needed to build the city’s most iconic landmark, the Duomo, the Navigli are part of Leonardo da Vinci’s legacy on the city. As well as being an artist, Da Vinci was an architect, engineer and inventor, brought in on the project to  link nearby Lake Como with Milan. Now, the Navigli are dotted with vintage stores, quaint little bookshops and trattorie – the kind with the red and white check tablecloths – serving up risotto allo zafferano. 

That’s another thing about Milan. Its food scene. Thanks to its international appeal and credentials as a financial centre, new restaurants are popping up all over the city to satiate an ever-expanding workforce. My latest discovery was Frangente, between the central station and Porta Nuova. Slick, stripped back modern interiors and a menu that sings. The old flavours of Italy, like stewed tripe and pappardelle al ragu are served up with a contemporary twist and vegetables are given the love and attention they deserve. I ate a bowl of veg here and wanted to cry, it was so perfectly cooked and seasoned. A stroll away, Mercato Centrale, a hip and trendy food hall has opened, touting fresh fish, cold cuts, pizza, pastries served up by ‘artisans’. It all smacks of inner-city gentrification but the produce and the end result are undeniably good. 

It wasn’t just the food that wooed me though. Old Milanese haunts have a charm about them that have me momentarily wishing I was Milanese myself. Bar Basso, opened in the 1950s and the birthplace of the ‘Negroni Sbagliato’ is one of these places. From its vintage red sign to its bold, cursive typography design stamped across the napkins that the bar’s famous negronis come served atop, Bar Basso is Milan distilled. The grand chandeliers, the pink panelled wooden bar, staff in white button downs and  smart clientele, all in a uniform of cashmere and monogrammed shirts; it’s all so impossibly glamorous without being pretentious. Effortlessly stylish with a touch of humour. 

This also rings true of the homes I’ve had the luck to be welcomed into in Milan. Great pieces of heavy wooden furniture are off-set with modernist light fixtures, designer Floss lamps juxtaposing antique bookshelves. Colours pop from unexpected places – the bright yellow cable of a light or a single statement wall of fuschia pink behind 19th century portraiture. I love colour and these things really get me. 

The Milanese know how to pull a look together, fashion obviously not excluded from this. It’s a city I know I can find great vintage clothing finds for relatively acceptable prices (Humana Vintage is the one). I bought a bright red and pink, reversible coat this winter from Wait and See boutique (stacked full of my favourite type of clothing, all clashing colours and popping patterns) and I’ve had people cross the street to tell me how much of a great coat it is. For shopping, Milan is unbeatable. 

A final note on the architecture. There are beautiful buildings in Milan, you only have to stroll around the pretty streets of Brera or the grand palazzi curving around Piazza Castello and Milan’s Medieval fortress to take in dramatic renaissance architecture with gigantic wooden doors that lead into secret courtyards. The city is best experienced on a slow, aimless stroll. It’s on these wanderings and meanderings that I fell for Milan. I stuck out like a sore thumb, between the suited slickers rushing between their morning espresso and work at ‘City Life’, but I appreciated Milan all the more for it.

Spots to fall in love with Milan…


  • Wait and See Boutique 
  • Humana Vintage 
  • Dieci Corso Como



  • Triennale di Milano
  • Mudec 




Eating out

  • Out of the Box Gelato
  • Trattoria Burla Gio 
  • Trippa
  • Frangente
  • Erba Brusca

Wait and See Boutique 

Humana Vintage

Dieci Corso Como

Triennale di Milano


Bar Basso

Bar Luce, Fondazione Prada

Out of the Box Gelato

Trattoria Burla Gio



Erba Brusca