Milan might not be everyone’s dream Italian city – but for us, it was the perfect fit. Seven days of curated chaos: Walking among couture and crumbling stone, searching for the perfect vintage leather jacket, and falling into that wonderful rhythm of espresso, pasta, gelato, repeat.
Before we even set foot in a boutique, Milan was already showing off. Antique trams clattering past old apartment buildings, and unexpected finds inside of parks including the stunning Arco della Pace (Arch of Peace) and the quiet Castello Sforzesco (Sforza Castle). Even when we knew exactly where we were headed, the city kept surprising us. It’s a place where everyday movement feels like a kind of runway.
When I think of fashion, three cities come to mind: Paris, Milan, and Tokyo. Well, I had a lovely time shopping in Paris the summer of 2017 and we’re headed to Tokyo this summer, but I can’t imagine either city holding a candle to Milan.
First off: The designers. I knew that Italy is known for its high-end clothing, bags, and shoes, but I didn’t realize how many brands were founded in Milan itself. Everything from Prada to Armani to Versace to Moschino to Dolce & Gabbana. And Rome and Florence do well for themselves as well with Gucci, Valentino, Fendi, and more.
And while everyone who visits Milan flocks to the Galleria for the photos and the architecture (we did too!), a few blocks away is where the Milanese do their shopping – Via Monte Napoleone. Which, in the fall of 2024, dethroned New York City’s Fifth Avenue as the world’s most expensive shopping street.
While we did plenty of window shopping, some of the stores were able to lure us in. Hermès was always busy. Valentino’s spring 2025 collection of purses is incredible – and they had the best customer service. Moschino will forever be memorable as the place I tried on the most bonkers runway outfit made out of denim (I walked away with a much more everyday style of jeans!).
Via Monte Napoleone isn’t just a shopping street – it’s a runway for cars too. At one point, a vintage Porsche drew more attention than the window display it was parked in front of. We even spotted what turned out to be Sfera Ebbasta, a Milan-born rapper, parked outside the boutiques, posing beside his Lambourghini while fans gathered. In Milan, the fashion isn’t limited to the clothes. (As an aside, Ebbasta’s collaboration album with Shiva dropped a few weeks ago and is dominating Italy’s music charts.)
We also visited a mix of local gems and global icons like Biffi Boutiques, Mimanera Milano, Gallo, Onitsuka Tiger, Adidas, and Ralph Lauren before diving into the world of vintage.
This is what we came to Milan for (well, that and the gelato!). We had a list of every vintage shop we could find in Milan and hoped to visit each one.
When we arrived, we were struck by how well dressed everyone was – and after seeing the prices in the vintage shops, we could understand why! If the designer shops have a street in Milan, then so do the vintage shops and we struck gold on Via Gian Giacomo Mora.
Our favorite vintage shops were Cavalli e Nastri and BIVIO – and lucky for us, both had multiple locations! I got to try on outfits I never would have imagined myself in – like Armani heels, Gucci dresses, Versace shorts, and more. Cavalli e Nastri stood out for their exceptional curation. Each piece felt intentional, beautifully preserved, and styled like it had already been plucked for an editorial shoot. But that kind of polish comes at a price – they were easily the most expensive vintage shops we visited.
BIVIO still had those stunner pieces, but you had to be willing to dig for them. That said, their Mora location was still pretty curated – and I got to walk away with a stunning new leather jacket to replace my previous Amsterdam market find from 2017.
Another standout was Live in Vintage, a place that felt less like a store and more like stepping into someone’s personal archive. It’s run by an older woman who knew every piece in the shop – designer, year, collection, and often the story behind how it came into her hands. She had some truly remarkable pieces, like a dress from Alexander McQueen’s final collection and a Louis Vuitton 100th anniversary bag with a wild backstory involving a yacht and a woman who insisted it simply didn’t “fit.”
We got to talking, trying things on, and I did end up buying a gorgeous 90s slip dress from an Italian lingerie designer (that she had just picked up the day before!) – but more than that, I left feeling like I’d met my adopted Italian nonna. She shared her secrets for spotting authenticity, walked us through her sourcing process, and was just…luminous. It was one of those experiences that made Milan feel personal.
Other notable mentions include Room37 (just around the corner from Live in Vintage), they had an incredible collection of jeans & Burberry jackets. As well as My Vintage Attire – if you want a vintage designer bag, this is the place to get it.
Of course, there were some misses for us as well – including the Naviglio Grande Antique Market, held the last Sunday of each month. The location along the canal was beautiful, but we were completely overwhelmed by the crowds and didn’t end up purchasing anything.
Not too far away were some wonderfully unique buildings, including one with a red, blue, and yellow mosaic facade. Seen below is the old leather jacket – but I’ll share a pic later on of the new one!
Before we dive into what we ate in Milan (and it was a lot), it’s worth mentioning that some of our favorite shopping didn’t involve clothing at all. Between Eataly, Peck, and La Cantina di Manuela (wine bar), we stocked up on everything we’d need to get us through the rest of our semester in Senegal – wine, olive oil, pasta, chocolates, and a few other pantry treasures. There’s something deeply satisfying about grocery shopping in Italy, like every shelf is curated with the same care Milanese boutiques give to their displays.
One thing that surprised us when we looked up menus in Milan – they don’t seem to eat nearly as much pasta as the rest of the country! That said, we still found plenty to indulge in. There was fast pasta at Pastificio PLIN – their homemade tagliatelle and potato & leek ravioli were sensational. Via Pasteria is a Milanese chain with three locations and they had fun takes on pesto fusilli and spicy spaghetti.
We also had found ourselves indulging in a few brunches, although we preferred the food and vibes at Hygge Corner over Horto Restaurant. Unsurprisingly, Hygge was incredibly cozy and I’ll be dreaming about their egg burger and smashed potatoes for ages. Horto, while being a Michelin starred restaurant, wasn’t quite our vibe, although Chandler admitted they had the best espresso in Milan. I, however, wanted French toast, not cake bread.
We also found an abundance of vegan/vegetarian restaurants and that is perhaps what we loved most about Milan. They had our favorite vegan fast food chain – Flower Burger – and we went back anytime we needed a quick meal. I think cherry bomb is our favorite burger, but it’s got some stiff competition! And their potato wedges are perfection.
Il Lughino and La Colubrina were the most traditional vegan restaurants we went to. Il Lughino’s menu was incredibly hearty and we feasted on quiche, lettuce lasagna (I promise it was good!), fusilli, and seitan steak. At La Colubrina we ate pumpkin risotto, a fascinating carbonara, and olive & caper pizza – their vegan cheese wasn’t bad.
Now, it would be impossible to pick my favorite Milanese restaurant. In the end, I narrowed it down to the top four. First there was Linfa, possibly the most varied menu, we ordered a bit of everything and were delighted. We happened to eat during their Sunday brunch, so we ordered beet toast and “save a crab” sushi for appetizers, cashew & truffle (yes!) gnocchi and bolognese (shockingly authentic) for mains, and matcha & pistachio cheesecake for dessert.
The Meet Milano probably had the smallest menu, so we ordered a good chunk of it with their shepherd’s pie, fettuccine, no-bake cinnamon roll, and brownie. Our interactions with the owner & the chef are what made this restaurant stand out. Every piece of furniture, glass, and dish was selected intentionally and half of the menu is dedicated to sharing their goal of being a zero waste company. They clearly have a vision and they love sharing it. If we found our long-lost Italian nonna at Live in Vintage, The Meet Milano felt like it was run by our hip, ethical older sisters.
There’s no such thing as too much pasta, but when we came across Nori Way, we had to stop in. Possibly the most authentic, yet funkiest, plant-based sushi restaurant we’ve ever dined at. Their menu forced us to over-order and we did not regret it! Standouts were the funghi oyster nigiri, tartufata uramaki, tosago & avocado gunkan, mango gunkan, and – believe it or not – tacos!
Which leaves Altatto Bistrot. This vegetarian restaurant required a reservation because it only has six tables. You can choose from the four-course or six-course menu and then each plate is an adventure. They paired it with one of the best bottles of wine we’ve ever had and the entire evening was magnificent. The only downside is that the restaurant isn’t particularly easy to get to, but it was absolutely worth the effort! I’ll be dreaming about their tempura ginger for the rest of my life.
But you can’t talk about Milan without mentioning gelato – especially since we arrived during what might be the happiest week of the year: Gelato Week. Naturally, I took this celebration as a personal challenge and made sure to eat gelato every single day.
Now, my absolute favorite scoop of the trip wasn’t actually in Milan (you’ll have to wait for my next post to hear about that surprise in Parma). But the crown for best gelato in Milan goes to La Romana. They make all their gelato in-house using natural ingredients, with a rotating schedule to ensure nothing is ever more than three hours old. When we visited, they were featuring some limited-edition flavors in collaboration with Ritter Sport, and I couldn’t stop going back for more of their carmello salato. It was that good.
Other wonderful mentions include pistachio at Vero, caffè at Chocolat Milano, and nocciola (hazelnut) at Out of the Box (they also had the largest vegan selection for Chandler).
Of course, no trip to Milan would be complete without visiting the Duomo. Yes, it’s enormous. Yes, it feels like you’ve stepped into a Gothic dream. But what stayed with me most wasn’t the interior – it was the terraces above, where the white marble spires stretch into the blue sky and the details reveal themselves one delicate carving at a time.
The Duomo itself is a wonder in more ways than one. It took nearly six centuries to complete, beginning in 1386 and officially wrapping up in 1965. Unlike the soft stone facades of Florence or Rome, Milan’s cathedral glows white thanks to Candoglia marble hauled in from quarries near Lake Maggiore. With 135 spires and over 3,000 statues, it’s a masterpiece of Gothic ambition that somehow never feels overwhelming – just intricate and endlessly fascinating.
Did you catch the new leather jacket?
From the terraces, the city unfolds in layers – traditional Italian rooftops in the foreground, giving way to sleek high-rises lined up along the horizon, a reminder that Milan is both ancient and unapologetically modern.
From the Duomo terraces, one building in particular caught my eye: The Torre Velasca. It rises above the rooftops like a Brutalist spaceship, perched on stilts. Built in the 1950s, it’s a relic of post-war architecture, meant to echo medieval watchtowers but with a distinctly modern, almost industrial feel. Some call it an eyesore; others, a masterpiece. I have to admit I became a little obsessed with it!
Just steps away, Galleria Vittorio Emanuele II rises like another cathedral – but one dedicated to fashion. Built in the late 19th century, and named after Italy’s first king, it connects the Duomo to the La Scala opera house. Its soaring iron-and-glass dome feels as grand as any museum, with intricate mosaic floors beneath your feet and light filtering in from above. Plus, more selfies than we’ve seen just about anywhere outside a US National Park! Not that we didn’t snap some photos and window shop with everyone else.
Both landmarks are worth every moment. But if that’s all you did in Milan, you’d miss the city’s true rhythm. The places where fashion spills out onto the streets, where lunch turns into gelato, and somehow a bottle of wine appears by dinner. The kind of days that don’t need planning to feel complete.
One thing we did miss – The Last Supper. We showed up without tickets, fully convinced we could just grab some on the spot. (Spoiler: You can’t. You need to book them weeks in advance.) Truthfully, neither of us was all that heartbroken. Religious art isn’t really our thing, and while it felt like something we should see, it wasn’t something we were itching to (hence the lack of planning). Still, I’m glad we wondered by the Basilica di Santa Maria delle Grazie where it’s housed – the building itself is beautiful.
Before we arrived, I worried that Milan would feel cold. all sharp edges and designer bags. People often describe northern Italy as more reserved, more businesslike – a contrast to the easy warmth we’ve felt in other Italian cities. But Milan surprised me.
Instead, it felt like a city with great taste – but also the willingness to share it. Milan ended up being one of our favorite Italian cities.
Abroad With Ashley 