Alessandro Schaffner: Moving to Amsterdam, Vintage Denim & the Hunt for the Perfect Watch

I first came across Sandro the way most of us discover people these days, through a screen, scrolling past photos of worn-in denim, obscure vintage chronographs and suits that look like they’ve stepped straight out of a family album from the 1950s. What caught my attention was the fact that behind every piece he wears there’s a story, usually a longer and more interesting one than any trend report you’ll read this year. Sandro is only 21, yet he talks about clothing, cars and watches like someone who has spent decades buried in archives. We talked about his move from Atlanta to Amsterdam, the smell of fresh basil that takes him straight back to childhood, and a two-year hunt for the right watch, and why he thinks true luxury is, above all, time. Here’s what he told us for our #ManoftheMonth series.

Can you briefly introduce yourself to our readers?

Alessandro Schaffner: My name is Alessandro, but most know me as Sandro. I’m a 21-year-old Italian American, born and raised in Atlanta. Right after graduating high school I packed everything up and moved to Amsterdam, a place I’ve now called home for three years.

“At my core, I love anything that can tell a story. I believe the present and future cannot exist without an understanding of what came before it. That’s why I like to regularly jump down the rabbit hole into the past. I love exploring the stories and lives behind clothing, cars and watches, those are my three pillars of interest, and the stories behind them are infinitely fascinating to me.” - Alessandro Schaffner

You’re only in your early twenties, yet your style feels remarkably timeless. What first drew you to classic menswear?

Alessandro Schaffner: As I mentioned, anything with an interesting story will always captivate me, and when it comes to classic menswear, those stories are damn near infinite. On top of that, who doesn’t want to look impeccable while wearing something full of history? I began collecting clothing about four to five years ago, and in the last three my passion for its history has grown tremendously. I didn’t start with classic menswear specifically, but it was inevitable that I’d come to realize the influence and history behind it.

I’m also a huge believer in “look good, feel good,” and there’s no better outfit that exemplifies that than a well-fitting suit. It’s the epitome of classic menswear. So it didn’t take long before I started searching outside genres like workwear and deeper into the world of classic tailoring.

How would you describe your personal style in three words?

“Wanting Grandma’s Approval.” - Alessandro Schaffner

Do you switch fragrances with the seasons, or stick to one signature scent?

Alessandro Schaffner: This is a tough one, because I don’t feel like I’ve explored the world of fragrance enough to say what my signature scent is. I’m honestly still on the hunt for it. What I can say is that scent, both in my own experience and in science, is one of the greatest triggers of memory.

However, one of his favorite examples is the smell of fresh basil. Growing up, his mom would always have him and his brother smell the basil she'd just picked while cooking, and to this day, whenever he catches that sweet, summery scent, he's instantly transported back to being a kid helping her in the kitchen. Because so many smells work that way for him, he likes to base his seasonal scent choices on the memories they trigger. He doesn't switch for all four seasons, but he does for summer and winter. In summer he reaches for something fresh and citrus-based, like Acqua di Parma's Colonia, it reminds him of days at the beach with his family, but also of his grandfather, since it was his cologne and his mom gave him one of his old bottles after he passed. In winter he leans into woody, warm scents that feel like a crackling fireplace, like Chanel's Égoïste, which he's worn for years.

What does your perfect day off look like?

“Something short, sweet, and meaningful.” - Alessandro Schaffner

Alessandro Schaffner: Waking up with my girlfriend to a cold winter breeze through the curtains, sheltering under a thick duvet before finally stepping into the cold, crisp room. Then getting dressed and heading to a proper, classic breakfast at some local, grandma-style diner, followed by a morning walk by the river or through the forest with our dog.

For lunch, we’d drive out to see family, winding down back roads until we’re greeted by the smell of parmigiana at the door, a scent that’s taken me back to childhood since I was a kid asking my nonna to make it, a tradition that continues to this day. After lunch, we’d sit around playing cards, Catan or Burraco. In the evening, an aperitivo with friends over a few not-so-serious games of billiards, then date night with my girlfriend: a dimly lit room, soft music, a crackling fireplace, hours of talking and laughing, ending the night bundled up under a blanket on the couch with our dog, watching a movie and having a sweet treat.

What fascinates you most about vintage clothing?

Alessandro Schaffner: I see vintage as a key to a door, opening into the past lives of those who made it and those who wore it. The clothing we have today is a byproduct of centuries of innovation, and exploring vintage is really piecing together the puzzle of how we got here. Something as “simple” as a down jacket can suddenly become part of a much bigger story once you learn about Eddie Bauer’s journey to develop the first commercial down parkas, inspired by soldiers who survived harsh winters in feather-stuffed jackets.

I also love vintage for the sheer amount of character it holds- Every stain, tear, repair and fade becomes part of a previous owner’s story. White strike marks along the thigh of a pair of jeans, for instance, can tell you the owner was a smoker who used to strike matches against the fabric. Certain repairs can even hint at where someone lived or what they did for a living. Once you’ve studied vintage garments long enough, you start to recognize their language, you can spot what a brand pulled from its archives for a new design, or date a vintage piece almost on sight, no Google required. To me, vintage clothing isn’t just something from the past, it’s one of the ways we can actually hold the past in our hands.

What’s one style rule you think people should ignore?

“Blue and black will always be a killer combo if pulled off correctly. I think people should be more experimental with color combinations in general, plenty of “rules” are really just warning signs because a combo can easily go wrong, but if you’re brave enough to figure them out, plenty of “no-go” pairings can work impeccably.” - Alessandro Schaffner

Has living in Amsterdam changed the way you dress or think about style?

Alessandro Schaffner: Definitely. Since moving here, my world has grown tremendously. I’ve found my own playground, full of people who want to jump in and make it fun. That means friends I banter with about vintage nearly every day, and shopkeepers I regularly visit, where catching up almost always turns into a conversation about style. Living here has taught me that personal style is much more than just the way you dress, it’s a form of self-expression, but also a door into a community of people who share your interests.

He professionally repairs vintage garments. He says it's taught him how much value people used to place on their clothing. He looks to old period repairs for inspiration, which showed him how differently people treated their wardrobes back then, most owned just a few combinations per season and took care of them accordingly. Take jeans: an estimated 4.5 to 6 billion pairs are made every year, almost enough for everyone to buy a new pair annually. But many of the jeans he collects were probably someone's only pair, worn for a decade or more. Every fade and repair tells that story, teaching him to appreciate both the quality of older garments and the mindset behind them, that clothing should be cared for, not thrown away.

What does true luxury mean to you?

Alessandro Schaffner: True luxury shows up in a lot of ways for me, but what matters most is health, family and friends, and time. Health, because waking up able to chase whatever I want is something that’s easy to take for granted. I was sick and stuck in bed just last week, and it reminded me how much I take being healthy for granted. Family and friends, because being surrounded by people who love and support you is something I’m endlessly grateful for. And time, I don’t enjoy feeling rushed, and I think a life with more freedom from that constant rush is close to the ultimate luxury, even if it’s a bit like a carrot dangling just out of reach.

What’s currently on your wish list?

“If we’re talking no-limit wishes, without a doubt a Ferrari 275 GTB, extra brownie points if it’s chassis #10669, the one once owned by Miles Davis.” - Alessandro Schaffner

Which watch in your collection has the best story behind it?

Alessandro Schaffner: That would have to be my 1940s Universal Genève Compur

Chronograph with Breguet numerals. For me, the epitome of what I look for in a watch: a simple design from one of the greats of watchmaking, with a few unique details. Finding Breguet numerals on a 1940s UG isn’t unheard of, but it’s a bit like finding a needle in a haystack.

The story started about two years ago, when I spotted the exact watch on Vinted one evening and couldn’t stop thinking about it for the next two or three months. After chatting with the seller and offering more money than I really had, I finally bought it and two weeks later it arrived, everything I’d hoped for, except I had no spring bars for it. It turned out to use “female” spring bars, with prongs on the lugs instead of the usual holes, which made sourcing replacements nearly impossible. After a week of searching every platform and shop I could think of, I randomly found a watchmaker on YouTube who had recently made a set for an almost identical 1940s Girard-Perregaux. I convinced him to make me a set too, but after months of waiting, they didn’t fit. He kindly bored them out slightly, and nearly a year after buying the watch, I could finally wear it.

Or so I thought. I’m also a big fan of beads-of-rice bracelets, and wanted a vintage one to match, but the watch’s 16mm lug width made that its own separate hunt. Weeks later, while buying an entirely different watch, I noticed the seller wearing the perfect bracelet on his wrist. He was reluctant to part with it, but after some convincing, and spending more than I’d planned it made its way to my door. The whole journey, from Vinted to the spring bars to the bracelet, made that watch far more special to me than it would have been if I’d simply bought it complete.

Which three books would you recommend to every modern gentleman?

Alessandro Schaffner: First, Black Ivy, one of the greatest style books ever written, an endless bank of inspiration I’ll always keep in my house. Second, Letters to a Young Poet, a great catalyst for introspection, which my mom introduced me to during my senior year of high school. And third, Winnie the Pooh, everyone needs a lighthearted read, and somehow this one manages to be exactly that while holding a lot of deeper messages; it’s also a book my dad often references, which makes it even more special to me.

Finally, what does being a modern gentleman mean to you?

“Live your life true to yourself, chasing your dreams and ambitions, but do it while treating the people around you the way you’d want to be treated, and without compromising your values and morals.” - Alessandro Schaffner

Quickfire Questions

One watch for life?

Alessandro Schaffner: From my collection, the UG Compur, the perfect, goldilocks chronograph. Or, dream collection, a 1950s Submariner, preferably ref. 6538: functional, historic, and a cornerstone of the watch industry, both elegant and rugged.

Favorite city?

Alessandro Schaffner: I have to keep exploring. I’m not sure I’ve found it yet.

Vinyl or Spotify?

Alessandro Schaffner: Spotify day to day, vinyl for date nights or special occasions.

Dear Sandro, thank you for this wonderful conversation, and we wish you all the best! See you in Amsterdam.

Photo: Alessandro Schaffner