Packing for any trip can be kind of challenging, especially in these days of more people trying to travel carry-on only. Packing for an Italy trip, however, is a whole other level of challenging – how are you supposed to fit weather-appropriate clothing into your suitcase that will also help you blend in among some of the world’s most fashionable people?
In short, you’re not supposed to. You can try, though, and there are ways to pack that will have you looking more like a local and less like a tourist. That’s a good idea not just because you’ll feel more comfortable in a crowd, but also because the less you look like an outsider the less appealing you may be to pickpockets who prey on travelers. So my advice is to focus on hitting that sweet spot of comfortable travel wear that looks good in Italy.
Don’t forget to consult my Italy weather page to find out what the conditions will be like during your trip!
Italians tend to dress up more often than many other cultures do, including for simple trips to the grocery store. You won’t catch Italians out in public in yoga pants or sweats unless they’re on their way to the gym, and this is not cutoff-jean-shorts country. (Those jeans you may see young Italians wearing, the distressed ones with all the holes? Those are designer jeans they bought with the holes already carefully created.)
I stick to one neutral dominant color for my travel wardrobe in Italy (my neutral of choice is black), and I bring a few colorful scarves along to brighten up the palette. I often end up bringing one semi-nice outfit, too, especially if I’ll be spending a good chunk of time in cities. That may mean a simple dress that travels well, or a pair of designer jeans with a sweater or nice top (not a T-shirt). The latter works as an overall guide for guys, too, though men can also bring a pair of slacks that travels well.
Italy used to be a country where I would hardly ever see shorts on anyone (except at the beach) in the summer, but that’s changed. Still, if you’re going to wear shorts, choose what you might call “dressy” shorts rather than the usual casual denim variety. Personally, I go with capris instead. And guys, don’t feel left out – capri-length pants for men have been really popular in Italy for years (they’re sometimes referred to as “man-pris”).
Note that most churches will require you to be more covered up than some of us dress in summer, so when you’ve got a church on your itinerary you’ll need to be ready with appropriate attire. Make sure your shoulders, midriff, cleavage, and knees are covered. Often, an oversized pashmina-type shawl will do the trick for the top half, ladies.
If you’re simply dying to know about the latest fashions in Italy so you can be “of the moment” the instant you get there, here’s my tip: prowl the outdoor markets for clothing stalls to see what color is everywhere, and then pick up an item or two in that color – a scarf is a great option, as it’ll serve as one of the colorful additions to your neutral wardrobe, or a shirt that you can easily wear a couple times during your trip.
Unless I’m going to Italy in the height of summer (or I know it’s going to be blazing hot the whole time I’m there), I typically pack a pair of boots (these are my current favorites, both stylish and extremely comfortable for all-day sightseeing), a pair of comfortable (and nice-looking) sandals (these are the ones I own now), and perhaps also a pair of walking shoes. I don’t even try to keep up with the fashions of Italian women who teeter on heels over cobblestones – I’d break an ankle in a heartbeat. (That doesn’t mean I don’t shop for heels while I’m there, it just means I wait to wear them until I get home!)
Younger generations of Italians are starting to get more casual with their attire, including footwear, but you still won’t see those seemingly ubiquitous rubber flip-flops unless you’re at the beach. Even casual sandals in Italy are nicer than the usual fare I see at home. Athletic shoes are quite common these days, but – like the jeans with the cultivated holes – they bear brand names, are sometimes a fancier version of what you might consider everyday shoes, and are usually spotless.
There are a few things that I like to pack almost regardless of where I go, and they’re all handy in Italy. Your mileage may vary with each one, depending on when you’ll be in Italy and whether your feet are as chronically cold as mine, but here’s my go-to list. I hope it serves as a starting point for your own packing must-have list.