Discover Milan in 5 Shops: Panettone, vintage Prada, and transformative wine

In our 5 Shops series, we guide you to our favorite independent retailers in some of the world’s most vibrant cities. From food markets to bookstores, vintage finds to local design, we've curated a diverse selection of shops where you can discover unique treasures.

While Milan is home to fashion giants like Giorgio Armani, Dolce & Gabbana, and the Prada brothers, the city's shopping experience extends far beyond haute couture—if you know where to seek it out.

As a travel writer residing here for over a decade, I continually explore for local treasures, whether it’s a vintage boutique nestled in a 15th-century palazzo or a cozy little bookshop in the heart of the city. Here are five spots that will take you away from the famous Quadrilatero d’Oro and introduce you to Milan’s independent shopping culture.

Top choice for souvenirs: Pasticceria Cucchi

Established in 1936 in the Ticinese district, Pasticceria Cucchi is a renowned bar, cafe, and pastry shop operated by the Cucchi family for three generations. This iconic Milanese establishment attracts stylish older women, fashion enthusiasts, and families alike for its croissants, coffee, and refined aperitivo (pre-dinner drinks) steeped in classic charm.

It's also the go-to spot for outstanding panettone (€40 for 1kg) available year-round. As the birthplace of this light, fruity cake, Milan offers the ideal gastronomic gift. I can personally attest to the cake's fluffiness and the subtle flavors of its candied fruits. For those short on luggage space, Cucchi’s also features gourmet nut spreads and irresistible chocolate-covered almonds.

Best spot for vintage finds: The Cloister

Vintage shopping in meticulous Milan is just as you envision it. Say goodbye to cluttered bargain bins; here, every item is chosen and showcased with incredible care. The Cloister exemplifies this. Nestled in a historic 1400s building, it’s located in one of Milan’s most picturesque neighborhoods (the Cinque Vie). The pieces are sourced from Italy and France, curated by vintage expert Daniela Cavero.

This is the perfect spot to find pre-loved Prada heels (€280) or a Valentino shirt (€210), though my personal favorite is the vintage workwear in various shades of blue (€80–230). On the upper level, explore independent publications with fascinating titles like Hiking the Dawn of the Metaverse.

Top choice for local design: Emil

Founded by Milanese designer Giulia Mojoli, Emil transitioned from an online store to a permanent location in the city’s Chinatown after six successful years. The shop is sleek, minimal, and as sophisticated as the women’s garments elegantly displayed on its racks. Every piece is crafted in Italy by local artisans, showcasing evident quality in both workmanship and materials.

Here you can find essential pieces for any woman's wardrobe, like a tailored silk striped shirt (€115) or sand-hued linen trousers (€142), both of which I nearly bought. If you're fortunate, the designer herself might assist you, sharing her enthusiasm for the products with genuine care.

Top spot for books: Colibri

Just a short walk (under 10 minutes) from the Duomo, Colibri is a charming bookshop-bar-cafe that checks all the boxes. It's conveniently located yet feels like a hidden gem, featuring a delightful courtyard adorned with plants and serving coffee that's as excellent as its gin and tonic. Most importantly, the bookshop is a thoughtfully curated space (albeit with a limited selection of English titles). It's the kind of place where you might buy a Virginia Woolf book and then engage in discussions about polyamory and politics with left-leaning friends from the nearby university. Interestingly, the building was once a squat frequented by Keith Haring in the ’80s, and it still features a mural he painted (though it's not accessible to the public).

Top choice for food and wine: Cantine Isola

Established in 1896, Cantine Isola has been a hallmark of quality wine and a friendly atmosphere for decades. Initially owned by the Isola family, it was taken over by the Sarais family in the ’90s, who have maintained its commitment to excellent wines.

What I adore about this enoteca is its warm and humble vibe. The shelves overflow with bottles from around the globe, complete with handwritten prices and even some poetry, while Luca behind the bar is eager to guide your taste buds. (He was nominated for Miglior Enotecario d’Italia – Best Wine Seller in Italy – in 2022.) Located in the heart of Chinatown, Isola is perfect for an evening of reasonably priced wine and snacks, or for discovering that extraordinary bottle.