One of the questions I often get asked by friends and family before they come over is, “What should I wear?” or “What should I pack?”.


I remember thinking exactly this the first time I came over to visit, and so, I packed my most stylish clothing, which, at the time, was nothing more than a nice pair of black leather walking shoes (because they go with everything – smart, eh?), nice T-shirts, jeans, and my Calvin Klein peacoat that I bought for $5 at Value Village just that year.

I won’t try to tell you that I was even the height of fashion in Canada, because as my girlfriends will attest, I dress(ed) horribly. I envied their way of always looking so put together and wished that I could be like that. But if I did invariably get them to come with me (they often insisted they accompany me) I would scoff at their choices until I could be convinced to try them on, and then I would proceed to buy one of each color so that I wouldn’t have to worry about doing THAT again anytime soon. But I digress…

So, you can imagine, when I landed in Milan, fully dressed in my western Canadian uniform of yoga pants and a hoodie (all LuLuLemon of course!) that I was beyond shocked. Thankfully, I wasn’t staying in Milan. I had another flight to catch to Pisa (Pisa Merda!).

Repeat. Land in Pisa. Shock and awe. Get in the car with my  “now husband” (is that how you could say that?) and drive to Viareggio.


I stayed in Viareggio for just over 2 weeks and I can guarantee that at every restaurant we ate at, every bar where we had a drink, and every church parking lot where we ate fried fish and partied (it WAS Carnevale after all) I felt like I was wearing the WRONG thing.

And the thing is, it wasn’t even my clothes that gave me away (though I’m sure that was a big part).

If you will pardon my mixed metaphor for a moment; Italians can smell a foreigner a mile away. In fact, so can most Europeans, but let’s stay focused for a moment.

It’s not just in the way we dress (sloppy, oversized clothing, and runners); it’s in the way we talk (loud and gregariously, and in English of course), it’s in the way we get incredulous that we can’t do things here in the same way we do them ‘at home’, it’s in the way we eat (coffee WITH dinner? A cappuccino after 10am?), in a nutshell, it’s EVERYTHING. The way we dress is just the icing on the cake.


But I tell you this, not so that you’ll think, “Why how DARE they!”, no, no. I’m telling you because this means that you don’t need to worry about impressing them, or trying to blend in, or feeling uncomfortable, none of that.

The advice I gave my own mother was to wear clothes you are comfortable in. If it’s hot, bring shorts and sandals that you can walk in a LONG time. If it’s cold, bring a jacket and shoes you can walk in a LONG time. Dress exactly how you would dress at home.

The most important thing you should think about is your shoe choice. Visiting a place like Rome will have you walking from morning to night with little rest. It will be glorious and you will want to pack up everything at home and retire here, but make sure your feet are comfortable. We recently spent a weekend in Naples and I left my stylish high-tops at home and brought my Asics instead. And my bunions are glad I did.

If I may offer another tidbit, think of this. Bring clothes you don’t mind sightseeing in. Ones that are comfortable, lightweight, that make YOU feel good. And then bring along something to wear for a nice dinner out. Stilettos with skinny jeans and a biker jacket are always classic. 😉

Don’t let your fear of being singled out as a straniera (foreigner) hold you back. You won’t be alone anyways, there are hundreds, no, thousands, no, tens of thousands of us here!

You’ll be in good company, I promise.