Rome in the rain

Henrik, hey. Sounds like a verrrrrry cool trip.

Thanks so much for writing in - and for being such a loyal reader. I’ve been doing this column for many years now, but you’re right, we really haven’t covered much in the way of footwear for Rome in the rain. Rome is one of those places I love... despite not having spent all that much time there. The ancient stuff will blow your mind. You’ll be walking down the street and turn down an alleyway and… whoa… is that the Pantheon?! I guess a lot of Europe is like that, but the casual presence of all that history, everywhere, is the coolest thing. So while I don’t know Rome well enough to tell you where to eat or where to shop (Yolanda’s got you covered on that,) I’ve spent enough time in virtually every other region of Italy to make some recommendations about what to wear to fit in and brave the elements.

You’ll want 3 pairs of shoes: a pair of leather boots with a Dainite sole (my pick is the Utah grain chukka boots,) a pair of Blundstones, and a pair of loafers. I know three seems like a lot, but those will cover all your weather conditions: Blundstones for when it’s really rainy, Utah grain for when it’s dodgy, and the loafers when the sun is shining. And it’s important to have some rotation — you never wanna wear the same pair of shoes two days in a row if you can avoid it. In addition to shoe trees, a day’s rest is the best way to keep your shoes in good shape for the long run.

The Blundstones are self-explanatory. These served as my snow boots during our years in Wisconsin and they can take any kind of sleet, rain, mud, whatever you might encounter on the Via Guilia. They’re treated to be water-repellent and the Chelsea-ish shape looks polished enough that you won’t feel like you’re wearing hiking gear. These can look very elegant with a pair of wool trousers.

Next up, the Utah grain chukkas. These were the first shoes that came to mind when I read your letter for two reasons: the skin and the sole. The Utah grain is a kind of textured calfskin that resists creasing quite well. I’m not gonna call it weatherproof, per se, but it'll be better in mist and drizzle than a suede or a very smooth calfskin because you won’t notice marks as easily (it’s also on the thicker side, as far as leathers go.) They’re Goodyear welted, which isn’t the most extreme kind of welting you can find — that would be a storm welt, which tends to look more casual, and Blundstones are gonna cover your most extreme weather cases here, anyway — but it’ll do pretty well in moderate rain. We went deep on GYW here, but short version: this welt, the strip of leather that attaches the upper to the sole, provides a layer of water repellency and insulation. And down the line, it lets you get more life out of your shoes by simply resoling them rather than buying a whole new pair. And then last up is the Dainite sole. It’s made of rubber, so it’s more robust than a leather sole, and it’ll give you some grip on those cobblestones thanks to the studded texture. The downside is that Dainite is on the heavy side compared to leather... but just wear them on the flight over and lighten your luggage load a bit. We do also make a Chelsea boot with the same Utah grain leather and Dainite sole, but I think the lace-up style of the chukka gives you more versatility if you’ve got Blundstones in the mix.

And then the loafers are just to switch it up a bit. Maybe you’re going to dinner and it’s dried out for the day; maybe the sun has come out; maybe you just want to give your boots a break. I’m more of a tassel guy, personally, but either pennies or tassels will get the job done… pick your poison. For December, I’d recommend socks. We have a wonderful assortment of boot socks right now for the other two, but with the loafers I’d keep it simple with neutral dress socks.

I know you’ve got clothes covered, but just in case, my quick list: definitely a blazer, a pair of 5-pockets, a pair of sport trousers (Bedford cord or high-ridge twill would be particularly good,) a pair of flannel dress trousers, some lightweight sweaters you can layer with (fine-gauge cashmere or Escorial), and a couple of shirts. For outerwear, you’ve got some options: the Traveler’s Trench is a home run because it’s water-repellent and looks pretty sharp (the insulated one is also fantastic)… but it won’t feel out of place when it’s not raining. But we’ve also just gotten this version of the Estate Jacket that I think would be fantastic. Same Cashpad (recycled cashmere) insulation, but with a tailored wool/cashmere shell that will make you feel pulled together (and safely out of the Gore-Tex territory you fear.) Adding a vest into the mix, if you have space, would also allow you to fit right in. The Italians love a vest.

Thanks again, Henrik. This sounds like a very special trip you’re taking and I hope your shoes can keep up. One more… footnote… (sorry) — when your letter came through, someone on our team immediately thought of this book, A Pilgrimage to Eternity, about a guy who took the thousand-mile journey down the Via Francigena and concluded in Rome at St. Peter’s Square. I’m not gonna call it a recommendation — I haven’t read it myself — but wanted to pass along the mention. Sounds like there may be some synchronicities with the trip you've got planned. Safe travels and enjoy.