First, an admission: @AnAcuteStyle is not in Italy. But when Arianna goes out of her way to describe a not-too-stuffy-but-still-put-together outfit suitable for aperitivo al fresco in late summer, I think it’s fair to bend the boundaries a little bit – especially when the outfit in question would be at home anywhere drinks are drunk and salty snacks are snacked.

My own experiences of aperitivo have been limited to my adventures at Pitti Uomo, and have largely taken in places patronized by men and women dressed much more nicely than myself (think of bars along the Arno, palazzos in the city center, and songstresses in floor-length gowns).  AAS would fit right in with that scene – much better than I ever do. That’s because his very East-Coast American look is both sharp and soft (yes, sharp and soft) enough to pass muster on the other side of the Atlantic as well. Strong roots, if you will.

I’ve always been a fan of blue-on-blue, and if you’re traveling for your aperitivo a sport coat in navy cotton is a fantastically versatile option that can be worn on the plane or with the collar turned up against an evening chill. When the weather starts to turn – chilly in the morning and evenings – I really like denim and chambray shirts for their versatility. They look good both under a jacket and alone, and with the appropriate weave you can get that lovely crunchy-cool-but-insulating feeling of a linen shirt.

The heavy tassel loafers and O-ring belt pull the outfit more towards the American than the Italian, but I think that’s why the balance works so well. Combined with a madras ball cap (I’ll admit I couldn’t find one in stock to link to), you’ll be ready to pursue Italy’s favorite pastime no matter where you are.

• Private White V.V. Ventile traveller blazer from Frans Boone
• Hickey Freeman tan wool traveler trouser
• Incotex chambray shirt from Mr. Porter
• Brooks Bros. tassel loafers
• Todd Snyder double O-ring belt
• Timex weekender
• Persol Sunglasses