This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.
Meet Alessandro Coltro (@alessandrocoltro), from Milan, Italy – the founder of Gents Cafe. With an appreciation for detail and timeless beauty, he set out on a mission to inspire a generation of modern gentlemen through a global, community-driven slow media brand that values authenticity, meaningful conversations, and the quiet ritual of slowing down.
Where do you live and what do you do for a living?
I live in Milan, and I’m the founder of Gents Cafe. If you’re reading this, chances are you already know what it is.
Gents Cafe reflects what I care about most: curiosity, depth, and a certain appreciation for the details that make life feel meaningful. I’ve learned more through this project than I could’ve ever planned for – from long conversations in DMs to unexpected friendships that started with a newsletter reply.
One of my favorite quotes says, “Your network is your net-worth.” It used to sound a bit cliché. Now I know it’s one of the truest things I’ve ever heard.
What are your main passions and how do you cultivate them?
I’m an endlessly curious person, which means I tend to fall in love with new things all the time. But a few passions have stayed with me over the years.
The first is building things, especially new ventures. I’ve always been a builder at heart. I love the momentum and excitement that come with turning an idea into something real—something that can have a tangible impact on people. I’m most energized in the early stages, when everything is still messy, uncertain, and full of possibility. I also find a lot of joy in bringing the right people into the process and shaping the project together as it grows.
Another passion that grounds me is CrossFit. It’s the only hour of the day where I can fully unplug. I love the structure, the challenge, and the no-nonsense mindset that comes with it. It clears my head and gives me the reset I often need.
And then there’s my deep love for printed matter—magazines and coffee table books, especially. I find something timeless in the charm of print. I love discovering new magazines on all kinds of topics, exploring how they tell stories and how they’ve been put together. The best ones are made to be kept, reread, and proudly left on a table—not just as decoration, but as a quiet way to say something about who you are. Being surrounded by them keeps me inspired, and whenever I need to spark an idea, I know I can go back to those pages.
That passion definitely carries into Gents Cafe. Even though we’re a digital media project, we try to bring the same level of care and thoughtfulness to our content—creating something that feels, as much as possible, like immersing yourself in a beautifully crafted printed magazine. I love it when people tell me they read our newsletter over the weekend, taking their time with a coffee or a drink. That’s exactly the kind of experience we hope to create.
How did you first develop an appreciation for style?
I have a vivid memory captured in a film photo my dad took when I was three. It was Christmas day of 1993, and in the photograph, I was sporting a jacket, waistcoat, striped shirt, bow tie, and a charming teddy bear pin on the lapel. Even though I can’t claim a passion for menswear at such a tender age, my parents have always had an influence on me in terms of caring about dressing well as a form of good manners. That mindset stayed with me, even as my style went through different phases. After university, I began to take it more seriously, shifting toward a more classic, timeless approach – one that valued simplicity, quality, and character over fleeting trends.
What does “being well-dressed” mean to you?
To me, being well-dressed means feeling completely at ease in what you’re wearing, and being in tune with the moment you’re in. It’s not about standing out, and definitely not about showing off. I’m not drawn to loud pieces or logos that beg for attention. What I appreciate are quiet details, the kinds of things that say something about you, without needing to raise their voice. It’s not about how much something costs. I’ve seen people look effortlessly elegant in clothes that wouldn’t turn heads on a hanger, but they own them. That, to me, is what makes someone well-dressed.
What’s a personal ritual that keeps you grounded?
Brewing coffee with a V60 every morning. It’s a slow, intentional process that I try not to skip. Grinding the beans, watching the bloom, hearing the water drip – it forces me to slow down. It’s a ritual I’ve only introduced recently, after asking endless questions to the barista at Cafezal – one of my favorite spots in Milan for a proper cup of coffee. He gave me a few tips, and after several mistakes (and a lot of overthinking), I finally found a way to make it work. I still have a lot to learn, but honestly, I’m okay with that.
Lately, I’ve also stopped checking my phone first thing in the morning. No emails, no Instagram – just coffee and breakfast, with no screens in sight. That quiet moment helps me reset. It’s a simple shift, but it sets the tone for everything that follows.
How do you define success, and what motivates you to achieve it?
To me, success means waking up and being free to choose how to live my day. It means working on ideas I believe in – but also having time for the people I love, for travel, for discovering new cultures, and for simply being present. It also means doing something that creates real value – not just noise. I want my work, in whatever shape it takes, to leave a positive mark, even if it’s a small one. I haven’t reached that version of success yet – but I know what it looks like. And along the way, I’ve realized that, for me, it’s not about status or numbers. It’s about freedom, connection, and building a life that feels honest – inside and out.
If you could have dinner with any historical figure, who would it be and why?
Adriano Olivetti, one of the most forward-thinking and unconventional figures of the 20th century. For those unfamiliar with him, he was an Italian entrepreneur, intellectual, and publisher who led Olivetti – an iconic typewriter and technology company known not just for its beautifully designed products, but for its humanistic vision of business. It was a company that built libraries inside factories and collaborated with some of the greatest architects of the time. I’m sure you’ve seen the iconic Lettera 22 model somewhere!
He believed that business could be a force for cultural and social progress, and that profit should be a tool, not the ultimate goal. He brought together ethics, aesthetics, and innovation in a way that still feels groundbreaking today.
One of his quotes has always stayed with me: “Utopia is often the most convenient way to dismiss what we lack the will, ability, or courage to do. A dream seems like just a dream until you start working on it. Then it can become something infinitely greater.”
His legacy is a quiet reminder that doing things differently is not only possible – but necessary.
What’s a challenge you’ve overcome that shaped who you are today?
I launched my first startup at 23, right after finishing my bachelor’s degree in computer engineering. Two years of intense work, naive optimism, and figuring things out as we went. Then we had to shut it down.
It felt like failure – because it was. I poured everything into it, and watching it fall apart was tough. But looking back, it was also one of the most important turning points in my life. It forced me to ask questions I had avoided: What did I do wrong? What did I ignore? What was I actually good at?
It taught me to detach my self-worth from outcomes – and that, hey, failure really is part of the journey to whatever success ends up looking like. It’s uncomfortable, yes, but it also clears the way for better decisions, more experience, and a clearer sense of what truly matters to you.
Since then, every project I’ve worked on has been shaped by that experience – not just technically, but emotionally. I don’t fear failure like I used to. I still don’t enjoy it, but I know I can get through it. That makes all the difference.
What are your three favorite hidden gems in your city?
I’m always on the lookout for new places to try—cafés, trattorias, and hidden spots in general. My saved folder on Instagram is getting quite long. But if I had to choose just three, these would be at the top of the list: Viastampa, Signorlievito, The Spirit
What are your three favorite movies?
