What to Wear in Italy in the Winter

Having traveled in Italy both in the summer months and the winter (and several points in between), I can say that it’s usually pretty easy to spot the tourists – no matter what season it is and what the weather’s like. And while I think packing a wardrobe that’s designed solely to fit in fashion-wise but isn’t practical for traveling isn’t the way to go, I do think there are ways to be a smart traveler who also looks good. I’ve talked before about my tips for what to wear in Italy in the summer, so here’s the flip side – what to wear in Italy in the winter.

At the outset I have to say that, as one expat friend puts it, Italians tend to dress more for the calendar than for the actual weather. As evidence of this, I’ve seen women in Milan bundled up in full-length fur coats and scarves in what I considered to be mild and even balmy springtime weather. I was surrounded by women like this, so I can tell you that they didn’t look the least bit overheated. This while I wasn’t even wearing a jacket. The bottom line here is that if you really want to look like a local in the shoulder seasons of Spring & Fall, that may require more layers than you think is really comfortable!

Many of the tips that I wrote about for the summer edition also hold true for the winter edition. This may be surprising to you, but if you think about it, it makes sense – Italian style is based on an overall aesthetic of looking good, which is something many travelers don’t bother with. But even if you’re the kind of traveler who’s content with wearing wrinkled clothing because it’s easier than asking for an iron at your hotels or hostels in Italy, there are some things you can do to blend in a bit more. And if you question why you’d even care about blending in, consider this – the more you stick out like a tourist, the more of a target you are for pickpockets. Enough said.

So, here are my tips for what to wear in Italy for a winter trip:

The rule against going “too casual” applies in the winter, too.
While you’re not likely to be sporting a pair of jean shorts in the middle of the winter, you probably don’t want to count on your convertible shorts-to-pants khakis to be good enough for a night out, either. Depending on the venue, a good pair of dark jeans will get you just about anywhere (and can be dressed up or down). For something a little dressier, you can’t go wrong with black slacks or, for the ladies, a black skirt. On top, skip the logo tees in favor of polo shirts, light sweaters, or some wrinkle-resistant button-down shirts or blouses. Shoes should be comfortable for walking, but I’d advise against those blindingly-white tennis shoes. Go with something black or brown (whatever the dominant color is in your suitcase). You’ll probably need a coat for the colder months, and a scarf isn’t a bad idea, either – but the scarf can be something you purchase locally, because pairing whatever a scarf in the latest trendy color with your neutral coat is a great way to look more like a local and come home with a great souvenir at the same time.
Black is the new… Black.
I know that there’s always a new color on the Italian fashion scene, something that “all the kids are wearing” and that you’ll see in every shop window in every city around the boot. But you absolutely cannot go wrong by bringing clothes from home that are almost exclusively black, or that go with the black elements of your travel wardrobe. It’s called “basic black” for a reason, people. And, as mentioned earlier, with a suitcase full of basic black you can pick up a scarf or sweater or whatever in that color you’re seeing in every shop window – it’s the perfect way to spice up a travel wardrobe without feeling like you need to bring your entire closet with you. Some people feel more at home in “basic brown” than black, and that’s fine – I’d just recommend sticking with one or the other. This not only helps you mix & match more easily, it also means you only have one color to think about when considering shoes and purses, etc., to bring with you.
Leave the backpack in your room.
Carrying a backpack, even a small one, around a city is one of the things that can make you really stand out as a tourist. Unless you’re carrying a bunch of camera gear that you need for the day, or on a day-long hiking trip somewhere and you need the pack for snacks & water, it’s a good idea to leave the backpack in your hotel or hostel room. This is actually much easier for women to do than for men, because we ladies have the ability to stick a few important items into a small purse (this is the one I use) and be ready for a day of sightseeing. Most men I know don’t carry a purse – but you may be surprised to see many Italian men walking around with bags that are somewhere between the size of briefcase and a purse. (If you’re so inclined, gents, you can pick up a nice one in the Florence leather market!) Guys, if you can get away without carrying around a backpack, that’s great – if not, at least be very careful with it in crowds and on public transportation.

For a couple more tips about looking like a local, see the post I wrote about what to wear in Italy in the summer – and remember, as I said earlier, you may find that the Italians look like they must be living in a much colder climate than the one you’re experiencing because they’re still wearing heavy coats and scarves when it’s sunny outside. Even as much as I want to fit in when I’m traveling, I’m not going to follow their lead on that one – I’d die of heatstroke. So, as with all things, remember to pay attention to your own personal comfort in this area!