I met Massimo Alba — founder and creative director of his eponymous label — 11 years ago in Milan. I was on a buying trip with my colleagues at Carson Street to London, Milan and Paris. Within moments of first meeting Massimo, I felt like I’d known him my entire life.
His clothes felt subtle, playful and reflective of a stylish and self-aware approach to fashion, which is to say they were beautiful and luxurious without taking themselves too seriously. The same can be said about Massimo himself. When you talk with him, he really listens, and responds thoughtfully and carefully. I’ve interviewed him a handful of times, and we’ve shared a couple of meals through the years. I’m lucky to call him a friend.
Back to our first meeting… It was at Massimo’s showroom, where he was previewing his latest collection. As a then-peon from South Brooklyn, I was happy just to be in that room with international creatives of all walks. Alba’s famed handkerchiefs hung on the walls, some with unique prints, others with witty or romantic phrases. The racks held luxury shirting, pants, jackets and outerwear, hung just-so, with enough space for the gathered buyers to inspect the finer details. Everything felt so luxurious, but not precious. It was an elegant, artistic take on classic menswear silhouettes. Everything was wearable. And that’s as true today as it was more than a decade ago when I first met Massimo and encountered his brand.
I reached out to Massimo last week to chat about how he’s dressing this season, what he’s currently on the hunt for and why he doesn’t feel regret.

What was the first moment you realized clothing can be transformative?
Clothes have always had this characteristic. They have the power to change people’s mood. They don’t necessarily change your attitude, but they can change your mood, your posture, even the way you move. There are days when I want to dress entirely in white, and others when I prefer blue. They are two of my favorite colors, and probably the ones I wear the most.
We’ve known each other a long time and I know you’re obsessed with footwear. What are you wearing this season?
I love the Bolina boat shoe we made with Fasciani. It’s made from kudu leather, and I wear it both in the city and when I’m on vacation. They’re currently completely sold out, but we’re hoping to bring them back for next summer.
What was your most recent purchase?
I bought a sculpture by Daniel Silver. A marble head. I like it very much.
Are there any staples you’ve found yourself rebuying?
T-shirts, for sure. I buy twelve at a time. Our Panarea T-shirts, specifically, in the colors I wear throughout the summer: white, charcoal and blue.
Is there one piece that you regret selling or giving away?
No, I’ve never regretted selling anything. Things come and go, and that’s perfectly fine. You have to know how to make room for something new. Otherwise, you end up living the life of a collector. I detest collecting. Collectors are often far too busy talking about what they buy.
What are you currently on the hunt for?
Partners to open new stores around the world. I’ve always dreamed of having stores in America: New York, by the sea in East Hampton, Los Angeles, Malibu. On a much more personal scale, I’m also looking for a fragrance. I’ve been searching for the right one for quite some time and I still haven’t found it.
What’s a hack you’ve learned about dressing for your build or complexion that you can share?
I would like to weigh practically nothing and be 1.95 meters tall. Unfortunately, that isn’t the case. I’ve become quite comfortable with my inability to remain the same size for very long, which is probably why I’d rather not give anyone advice on the subject.
Favorite place to shop in Milan?
For food, ça va sans dire. And I enjoy Antonia. They have a very good selection of fragrances, and the people who work there are always very kind. I think it’s one of the most well-balanced stores in Milan when it comes to both menswear and womenswear. I’ve also always had a very keen eye for design, and recently I’ve been really interested in what IKEA has been doing. I think theirs is a very interesting project. I particularly love some of the new limited-edition lamps.
One non style question for you: What’s a song or album you can’t stop listening to?
“E Ti Vengo a Cercare” by Franco Battiato. And “Stranizza d’Amuri,” also by Battiato.
The world of men’s style, from the streets of NYC to the showrooms of Milan, run down weekly by writer and photographer Christopher Fenimore.