
I landed in Rome the day the Pope died. I’m not a Catholic, but I’m also not immune to understanding the significance of that moment, nor can I ignore that it was a special thing to find myself in Rome, the home of the Holy See, on that day. It’s hard to think of a more relevant place to absorb news of that magnitude, but before I really had time to process the day’s most significant world event, I found myself on another plane, forgoing one pilgrimage site for another: Milan.
If Rome makes a compelling case for itself as the world’s capital of Christianity (it is, after all, the literal home to the capital city of the Catholic Church), Milan makes a credible claim to being the world capital of design and style. Alongside Paris, London, and New York, Milan is broadly considered one of the world’s most important homes of fashion. Gucci, Prada, Versace, and Armani all claim the city as their home (as opposed to countless other brands), and the city — which is just 50 km from Switzerland and a three or four-hour train ride from Geneva — has long been a center of watch collecting.
Northern Italy deserves a lot of credit for the modern state of watch collecting. A remarkably dense population of collectible watches have concentrated in Milan and the surrounding cities since the fall of fascism after World War II, and Italian collectors have staked a strong position in contemporary collecting, be they incredibly visible collectors like Auro Montanari (better known as John Goldberger) or up and coming creators like Andrea Casalegno (@iamcasa).

I was in Milan courtesy of D1 Milano, the rising Italian brand best known for their polycarbonate integrated bracelet watches, which aim to blend a decidedly upscale look with a playful attitude and sense of irreverence, mostly to great success. Ostensibly, I was in town to explore the brand’s latest F/W collection, coming later this year (and teased recently at Windup San Francisco), but I touched down in Milan with a different goal: To take my 48 hours and try to get a sense of what it is about this place that has made it such fertile ground for style and design (well, that, and to eat as many good meals as possible).
Arriving in Milan
Broadly speaking, in my experience, there are two sorts of press trips. In one bucket, you have the all-encompassing trips, where a brand plucks you out of your day-to-day life and drops you into a whirlwind adventure, one often tied to an extraordinary, once-in-a-lifetime experience of some kind, like Garrett’s trip to the Canadian Rockies last summer. In the other bucket, you have trips like this one, where a brand brings you to some far-flung city, and seemingly throws open the door, leaving you time to explore. For me, these trips are all about creating context. And there’s no context quite like Milan.

There’s an old line that Americans can’t quite understand how old things are in Europe, and Europeans can’t quite understand how far apart things are in the US. It’s surely an oversimplification, but the core idea is absolutely right. As an American, it’s hard to explore Europe without being struck by the history around you. Milan isn’t a city that was planned by someone’s great-grandfather; it evolved and expanded over centuries.
You can feel the difference. I’ve lived in some of the oldest cities in the United States, and they’ve got nothing on even the youngest major European city. In Milan, which has been continuously populated since before the Roman Republic, the history is palpable, something which was immediately clear from the moment I stepped out of my hotel on my first day in the city.

On the first day, I left the hotel with two distinct goals. The first of these was to keep myself awake until dinner — a semi-futile attempt to stave off the impact of jet lag on what would be my shortest European excursion ever — and to find my way to the iconic Duomo di Milano. On my way out I’d asked the hotel concierge for directions and had been given, at best, loose instructions. Actually, it’s better described as loose instruction: When you leave, turn left and keep walking.
As it turns out, that vague direction was all the instruction I needed. Assuming you start off headed in the right direction, Milan has a way of pulling you towards its center, so it was without too much trouble, and after a surprisingly short walk, that I found myself standing in the shadow of a truly immense cathedral.

The Duomo di Milano (or Milan Cathedral) is an awe-inspiring structure in the truest sense of the word. It’s the largest church in Italy, and the third largest church in the world, out-scaled only by St. Peter’s Basilica in Vatican City (which, though surrounded on all sides by Italy, is not technically in Italy) and the Cathedral Basilica of Our Lady Aparecida in Brazil. Now, I’ve never been to Brazil, but I have been to St. Peter’s Basilica, and while it may be bigger, head-to-head, it can’t match the visual presence of the Duomo di Milano. The free-standing cathedral overwhelms the senses, filling your entire field of view, despite seemingly rising out of nowhere.
It’s also a testament to enduring commitment, which I suppose is the point of any church. In a world where we expect mega-skyscrapers to go up in what feels like days, it’s hard to fathom a building that took nearly 600 years to finish — so long that, after The Great Wall of China and Cologne Cathedral, its the longest construction project on record (even the notoriously long-built Sagrada Família can’t hold a candle to it on that front). Of course, on paper, it would be hard to justify any sort of construction project that long, but in person, the impact is undeniable.

And the energy around the cathedral was undeniable, too. Maybe it was because the Pope had passed, maybe it was because it was the Monday after Easter and the city was half shuttered, or maybe it was just because it was a beautiful April day, but the Piazza was alive in a way that’s rare to see. Everywhere you looked, tourists and locals were milling around, enjoying one of those perfect days that seem to wake everyone up, even those of us who wanted nothing more than to crash into our beds.
Besides the Duomo, similarly grand, but far more modern (relatively speaking) and built as an ode to an entirely different sort of piety, sits the Galleria Vittorio Emanuele II. A palace-like remnant of the 1800s, the Galleria is Italy’s oldest continuously active shopping arcade. It’s here that you’ll find the Milanese boutiques of Rolex, Louis Vuitton, Gucci, Chanel, and Prada, nestled between packed restaurants and tourists just trying to spend some time in the incredible space.

All in all, it’s an overwhelming experience, and after a leisurely lunch (something the Italians are very good at facilitating), it was time to find some quiet. Thanks to a recommendation and a little quick map work, I quickly found myself in the gardens of the Villa Necchi Campiglio. Built in the 1930s for a prominent Milanese family by architect Piero Portaluppi, the Villa Necchi Campiglio is a true oasis in the heart of one of the world’s busiest cities. Just walking through the gardens is a tonic to the crowds found in the more visibly public spaces of the city, and the house itself is a treasure, balancing the ornate instincts of the city with a distinctly early-modern sensibility. If I were to offer one recommendation besides the obvious in Milan, this would be it.


D1 Milano
As much as I had enjoyed wandering aimlessly around Milan, I wasn’t just in Italy to explore, I was there for what D1 Milano was calling their first annual D-Day event — a blend of workshops, presentations, and new watches meant to give us a sense of the brand’s direction. So after an admittedly slow start to the morning, I found myself walking from my hotel to D1’s nearby offices, slightly unsure of what to expect. What I found was another oasis tucked away in the heart of the city, and an enthusiastic and excited team eager to share the story of the brand, as well as a lot of very cool watches.

After a presentation from D1 Milano founder and CEO Dario Spallone, we were moved from station to station exploring different facets of D1 Milano’s process. We swapped Milan-specific UV-printed dials into D1 Milano’s signature Polycarbonate watches, learned how to mix glow-in-the-dark resin from a doctoral candidate (whose post-graduate work includes collaborating with D1 Milano to push their material science), and played around with screen-printing — a shockingly satisfying technique, and one that had a room full of journalists and influencers giggling like kids in art class.


Most importantly, we got to see the new watches. D1 Milano has been around for a minute now. Dario founded the brand in 2013, and in the years since, they’ve made a name for themselves with well-designed, cheeky, fun, and affordable watches. But don’t call D1 Milano a watch brand. While D1 Milano certainly makes watches (and by all accounts, they make a lot of them — well over 100,000 a year, per the brand), they’d prefer to describe themselves as a design brand. And they do love design. Walking around their offices, it’s hard not to be struck by just how many sources they draw inspiration from. Model cars, Jeff Koons balloon dogs, and design books sit on iconic IKEA shelves, and every object in the space oozes intentionality.

I have to admit, until this trip, D1 Milano wasn’t a brand I really ‘got.’ But hearing from the team behind the watches, experiencing their world, and seeing the next evolution of the brand in person, they’ve earned a convert. D1 Milano doesn’t shy away from its sources of inspiration, nor does it take itself too seriously. Dario even called out the brand’s intention to create “toy watches” meant to evoke the form of some of the watch world’s true heavy hitters. And they’ve done just that — watches like the “Sketch” live in watch boxes side-by-side with their sources of inspiration, and don’t feel even a little out of place. And that’s because the watches, for all their lightness and humor, exhibit the same intentionality as the spaces they were conceived in.

After several hours spent exploring the world of D1 Milano, we all went our separate ways, breaking for an afternoon drink, more time spent walking around the city, and some downtime before seeing D1 in a new context: an art gallery. For a brand with a focus on design, there are no better collaborators than young artists, so D1 Milano engaged students at a Milanese art institute to create a series of interactive and visually arresting art pieces meant to highlight the new watches. In many ways, it was the perfect sign-off to the day, and I have to admit that I got an immense amount of joy from swinging a mallet down at a piece of stone only to have a watch reveal itself underneath.


A Melancholic Departure
My last day in Milan was a short one, but with a ride to the airport looming, I knew I wasn’t done with the city. So I wandered out one last time. This next line may sound trite or entitled, but it’s also true: there’s nothing quite like the feeling of wandering through a European city on a nice day with a Leica hanging from your shoulder. No matter where you turn, there’s something to see, and I could have spent weeks roaming Milan, filling up memory cards with the never-ending sights of the city.
I’m really glad I went out that morning, too, because there was one last thing I knew I couldn’t miss. So I walked out of the hotel and made my left turn, moving toward the now slightly more familiar Duomo di Milano. But when I got there, I didn’t stop. Instead, I kept moving, turning onto one of the main avenues of Milan, and kept walking until I was greeted by the Castello Sforzesco, a monstrous medieval fortification less than a mile from the Cathedral.

I love any old castle, and Italian castles are a breed unto themselves. They just have a look about them, one totally distinct from the Anglo-Saxon, Arthurian castles we’re so familiar with from movies and TV shows. They prize space and openness in a way the cold castles of Scotland or Wales just don’t, something reinforced by seeing them on a beautiful day, like I was lucky enough to in this case.

Still, just as soon as I’d gotten a taste of the castle, it was time to head back. Meandering back toward my hotel, I stopped for one last treat, a Stracciatella gelato — a combination of plain milk ice cream and chocolate drizzle that’s been a favorite of mine since childhood — and relished my last minutes in Milan, while simultaneously making plans for my next trip to the incredible city. Well, and thinking about how grateful I was that I didn’t need to fly through Rome again on my way home. D1 Milano