Menswear Vacation Style Guide: What to Wear for a Riviera Vacation

Let’s get one thing straight, gents. When it comes to embodying that rarefied sweet spot of money-drenched indolence without looking like a try-hard nouveau riche buffoon, nobody does it better than the Riviera’s sun-bronzed aristocrats. These tanned overlords of Mediterranean sprezzatura have mastered the art of blending tailored Italian luxury with an audacious streak of seaside rebelliousness. It’s a deliciously contradictory aesthetic that can leave you wondering: is he a rebellious artist who stumbled into an eight-figure trust fund, or a scion slumming it as a bohemian beach bum?

Their secret lies in an almost preternatural ability to appear simultaneously disheveled yet impeccably composed. It’s an exquisite dance of tension, teetering between studied nonchalance and laser-focused intent. Get too polished and perfect, and you’ll quickly be sniffed out as the former—a desperate social climber reeking of new money trying hopelessly to emulate old-world aristocracy. But get a little too unkempt and ramshackle in your pursuit of that romantic Tom Ripley allure, and bam—you’ve devolved into actual derelict territory (which, to be fair, is a vibe some particularly jaded trust fund burnouts aim for during peak Riviera debauchery seasons, like Cannes yacht week).

No, true mastery requires an almost spiritual understanding of when to lean into bold statement pieces that tantalize with beachy irreverence, and when to step back and let sleek, quiet luxury do the talking for you. It’s an intricate choreography that juxtaposes rakish, devil-may-care insouciance with a whisper of refined European sophistication—hinting at the generations of cultured, globetrotting bon vivants in your lineage.

But nail that deliciously contradictory sweet spot, the magical equilibrium between continental dignity and anything-goes Riviera spirit, and you’ll unlock the ability to command envy from the hardwood decks of Monaco’s sweeping harbors to the bougainvillea-draped, winding footpaths of Positano. A mastery of refined style that simply cannot be purchased, only inherited from generations of European ease.  So review our picks and pack wisely, for the intoxicating shores of the Mediterranean rivieras demand nothing less than sartorial perfection.