Hey Jason. Thanks for writing in.
We get several of these questions every summer… ‘tis the season to vacation in Europe. I have been traveling to Italy several times a year for about 30 years at this point, so I have the packing list pretty dialed in. Mine skews a bit more business than pleasure personally, but I’ve adjusted my advice slightly for the average vacationer – fewer suits, more shorts — and last summer we ran a column with the definitive Italian vacation packing list. That should be a solid foundation whether you’re there for two days or two weeks, city or country or somewhere in between.
And there shouldn’t be a huge difference between the two. In a bigger city like Rome, I might step it up a bit more and skip the shorts, but in a smaller town, like San Gimignano, you can get away with them. The locals are wearing soccer jerseys to the pizza place, you know? Everything is a touch more casual, but still quite refined. I was just there very recently and actually packed a bit more casually than usual since it was over a holiday weekend. (My tennis shorts even made it to the court – I got to play on the clay at Via Reggio and it was super cool.) But yeah, all the stuff in that column still holds. Pique polos, dress shirts as sport shirts, white jeans, navy blazer… I wore the heck out of my Ghost.
So, Jason, follow the advice in that column and you will be set. I will tell you a couple of pieces from this season that would be great adds on top of everything listed there:
Butcher Jacket in Lovat Lightweight Canvas. This jacket is a killer... will make you look like a local.
Spread Collar Sport Shirt in Riviera Stripe Chambray. Will look great under that jacket and a navy Ghost and on its own. You can tell by the name it's perfect for vacation.
Button Down Sport Shirt in Light Pink University Stripe Oxford. Slightly Tom Ripley, in a good way. The fabric will wear super well and the stripe has a little zip to it without standing out too much.
Marquez Shirt in Light Blue Seersucker. If you must leave your shirt untucked, at least make it this one, which is designed for that. The texture is fantastic.
Short-Sleeved Polo in Coastal/White Striped Jersey. You need the basic solids - navy, pale pink or pale blue – but a stripe is a nice add.
Slim Straight 5-Pocket Pant in Stone Bedford Cord. A sub for white or natural jeans that are a touch lighter in weight – there’s not a lot of A/C in Italy —and gives you a bit of texture.
Field Short in Vintage Khaki Canvas. The fabric of these has a bit more structure to it and will hold up well over multiple wears.
Swim shorts in the length of your choice… although you’ll blend in more in the Standard Length. Who wears short shorts? The Italians do. I personally go for the navy, which basically deserves an honorary stripe on the Italian flag.
Driving Moccasin in Bourbon Leather. The Italians love a moccasino. These are especially handy since the whole bottom is rubber – unlike most of the ones you see – so they’ve got some all-wheel-drive-ness to them. Great for cobblestones.
The Italians also love a trainer. I’d go for the perf if you want something more refined, the Tretorn Nylites if you like something sportier, and Diadoras to split the difference. All three will go great with a jacket.
An extra tie is nice to have if you go to dinner or something.
Buon viaggio, Jason. It’ll be great.