Milan-based watch influencer Andrea Casalegno shares his must-have timepieces, from everyday Rolex classics to vintage family heirlooms. Discover six essential watch categories that blend Italian style with universal appeal.
When it comes to watches, Andrea Casalegno brings the kind of infectious enthusiasm that only comes from genuine passion. The Milan-based influencer and GPHG Academy member has built his reputation on storytelling, finding the human connections and cultural threads that make timepieces meaningful beyond their technical specifications. His selections reflect a distinctly Italian sensibility: elegant without being flashy, thoughtful without being pretentious, and always with an eye for the stories that matter.
In this edition of Must-Haves, Andrea shares six watches that span his collecting philosophy. From Swiss icons to Italian diving legends, each piece represents not just excellent watchmaking, but the kind of versatile, story-rich timepieces that form the backbone of any serious collection.
Shop the entire collection of Andrea's picks here.
The most versatile watch ever–at its best with a classic silver or black dial. You simply can’t go wrong with a Datejust, and it's an absolute strap killer. In its 36mm form, its proportions are perfect, and it works with everything from suits to weekend casual looks.
One of the few dress watches that’s perfectly at home with denim and a t-shirt! Built on the golden ratio, it's pure mathematical poetry on the wrist. This is the peak of understated luxury, and challenges conceptions about what a dress watch can be.
It's iconic, it's still semi-niche, it's still a talking piece, and I love it. A real tool watch with a genuine story that separates it from a mere conversation starter.
I love the Conquest. Mine is my step-grandfather's, purchased in Caracas where he went to make his small fortune. This isn't just a watch, it's family history on my wrist. Every piece should have a story worth telling.
While everyone chases the usual suspects, I prefer the true legends of professional diving. Aggressively bold engineering that was built for actual divers, not desk divers.
No need to explain why! Some watches transcend rational explanation and they simply are. These are the pieces that make your heart race, that remind us why we started collecting in the first place.
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