Travelling to Milan? Your fashionable guide to Italy’s most stylish city

17 August 2023
By Henry Khov

Italy’s best-dressed city never goes out of style. Follow in writer Jessica-Belle Greer’s well-shod footsteps through her experience of its sartorial, artistic and gastronomic high points.

A fashionista's guide to Milan by Jessica-Belle Greer

As one of the world’s most important fashion capitals, Milan is a must-visit metropolis for any follower of fashion. Although for reasons you can read in the history books it missed out on being Italy’s actual capital, the Milanese traditionally consider it to be the country’s ‘moral capital’ for its cultural and economic contributions. Exploring its polished palazzos, esteemed steeples and modern architectural additions, it’s clear this is a city of significant creativity and spirited confidence. Shopping is, of course, a lifestyle choice here, but there are also many other aesthetic activities that can make your trip the most fulfilling — and fashionable.

A fashionista's guide to Milan by Jessica-Belle Greer
La Dinascente Mozarella Bar.


A stylish neighbour of the Duomo di Milano, the La Rinascent shopping complex takes its central position in the ‘city of fashion’ seriously. Curating a range of the latest designer collections across its soaring floors, it’s remained at the cutting edge for more than 150 years. If you’re short on time or simply want to assess all your options, it’s the smartest way to shop. In the food hall, Maio Restaurant and Obicà Mozzarella Bar let you dine with the divine courtesy of their views over the Duomo and almost saintly dedication to Italian cuisine.

A fashionista's guide to Milan by Jessica-Belle Greer
Duomo di Milano, photo by Jessica-Belle Greer.


Much more than a mall, the Galleria Vittorio is one of Milan’s major landmarks. The 1800s arcade is named after the first King of the Kingdom of Italy, but has picked up a nickname along the way —
Il salotto di Milano, Milan’s living room, due to all its comings and goings. It was under the central, glitzy glass dome that luxury fashion house Prada was opened as a luggage store in 1913 by Miuccia Prada’s grandfather, Mario. After impressing its noble visitors, Prada was appointed the Official Supplier to the Italian Royal Household, and incorporated the knotted rope design from the House of Savoy’s coat of arms into its logo. Like its enduing insignia, Prada’s store at the Galleria Vittorio has kept much of its finery, including the blackand-white checked marble tiles and mahogany shelving. When you step inside, it’ll seem surprisingly small, but that’s because the real retail experience is downstairs in an elegant hidden emporium. This writer found her way here near closing time, and took so long to decide which tote to take home, she ended up having the store to herself, thanks to a very gracious sales associate.


Follow the mosaic tiles of the Galleria Vittorio and you’ll find another famous storefront, Pasticceria Marchesi. Since 1824, at its historic outpost on Via Santa Maria alla Porta, the pastry shop has served dessert delicacies, including their perfected panettone, with sophisticated service. If you don’t get to take home your dream bag at Prada, at least this stop will make your outing bittersweet.

A fashionista's guide to Milan by Jessica-Belle Greer
Marchesi Galleria, photo supplied.
A fashionista's guide to Milan by Jessica-Belle Greer
Fondazione Prada , photo by Bas Princen


Fashion and art are inextricably connected in Milan, and nowhere is this more on show than at this cultural institution, situated in a former distillery in the Largo Isarco industrial area. Architectural
complex Fondazione Prada is state of the art — even the coat-check and bathroom seem like experimental installations, so modern and seamless are their design, and a favourite feature is the Haunted House, the exterior of which is covered in gold leaf. Inside, you’ll find work by emerging and established contemporary artists in an exciting line-up of exhibitions. Offering irresistible refreshments and cakes, on-site Bar Luce was designed by film director Wes Anderson, in homage
to ’50s and ‘60s Italian pop culture and Neorealism cinema — and the result is a movie-worthy masterpiece. On the sixth floor of the imposing tower building, Restaurant Torre offers views over South Milan, but you’ll spend most of your time admiring the warm walnut carpentry and hemp panels that cover the walls in mesmerising forms. The restaurant boasts the best of regional Italian food, and I can recommend the ‘secret’ off-menu green salad after what will likely be days of decadent pasta.

A fashionista's guide to Milan by Jessica-Belle Greer
Ristorante Torre


The most in-demand reservation in Milan is not at a restaurant, but at Leonardo da Vinci’s Last Supper. Being one of the most famous frescoes in the world, you’ll need to book weeks in advance to get an entry time to the dining room of the former Dominican convent of Santa Maria delle Grazie, where it’s located. The forward-planning is worth it, though, because given the artwork is painted on the wall, you’ll never see it on show anywhere else.

A fashionista's guide to Milan by Jessica-Belle Greer
Dior Salone del Mobile, photo by Adrien Driand


Once a year, the world’s great minds of design descend on Milan for the Salone del Mobile. Also known as the Milan Furniture Fair, it’s set the global benchmark for furniture design since it was established in 1961, and continues to surprise and delight. Celebrating personal style in our most personal spaces, it blurs the boundaries between art, design and fashion, with notable local exhibitors including Missoni, Versace, Fendi and Gucci. Held in April this year, the fair often inspires the whole city to participate, with satellite sites and many retailers putting together limited-time showcases in their own stores.

A fashionista's guide to Milan by Jessica-Belle Greer


Whereas many of Milan’s luxury boutiques focus on the new and next, the Naviglio Grande Antiques Market (Mercatone dell’Antiquariato del Naviglio Grande) holds onto what has gone before. Along Milan’s oldest canal, the Naviglio Grande, the nearly 2km route from Viale Gorizia to the bridge on Via Valenza hosts more than 380 exhibitors. Open on the last Sunday of every month, each stall is carefully selected and inspected to ensure high-quality shopping, including furniture, porcelain, silverware, glassware, watches, jewellery, books and prints. There are also many other stores, art studios and eateries to check out along the way.


Milan is forever welcoming world-class exhibitions, which are worth visiting not only for the prints and paintings, but also for the storied walls they hang on. From March to June, L’eredità di Helmut Newton presents a retrospective of the late, great photographer’s work at the Palazzo Reale, a former (and very impressive) palace that has become a cultural centre. From March to July, Dalí, Magritte, Man Ray & Surrealism: Masterpieces from the Boijmans Van Beuningen Museum will be hosted by the Mudec Museo delle Culture, which is housed in a building that’s surreal in itself.

A fashionista's guide to Milan by Jessica-Belle Greer


Going back to your hotel for the night needn’t mean the cultural tour stops. In the design district of Brera, dotted with luxury boutiques, art galleries, antique markets and cocktail bars, Casa Baglioni has
drawn inspiration from its surroundings for an immersive and impeccable stay. Intimate in size, the 30 suites and guest rooms are designed by Milanese architects Spagnulo & Partners to reflect a golden era of Milan culture, the ’60s, and the interior is embellished with works by important artists, including Enrico Castellani, Christo, Carla Accardi and Agostino Bonalumi. The Casa makes one feel at
home at Sadler Ristorante by Michelin-starred chef Claudio Sadler. 

Seating only 36, the dining room serves traditional dishes with contemporary accents, complemented by wine from the hotel’s cellar. A stay at Casa Baglioni is a chance to unlock the hidden corners of
Brera via private tours organised by the hotel, including one of the nearby influences of Italian architect Gio Ponti. Because art doesn’t exist in isolation, this hotel has already become a meeting point during Milan Fashion Week, which will take place in September.


Through an ornate Baroque gateway, you’ll discover the city’s newest hotel in one of Europe’s oldest seminaries. Renovated by architect Michele Bönan, this latest incarnation centres on classic Italian design, with meticulous attention to detail, sumptuous materials and a focus on the interplay between texture and colour. Owned by Ferragamo (through the Lungarno Collection), the 73 suites and rooms hark back to the stately mansions of Milan’s past with the refinement only a five-star hotel can achieve. Portrait Milano’s restaurant, 10_11, is inspired by the culinary traditions of Northern Italy, while the
corresponding bar continues the evolution of aperitivo, a Milanese ritual. This hotel is situated by the Piazza del Quadrilatero, the largest public square in the luxury fashion quarter. Between its historic
colonnades, you’ll encounter exclusive boutiques, among them the buzzed-about Antonia and So-Le Studio. It’s another kind of school for divinity, but perhaps no less enlightening.


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