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This article isn’t for the average woman traveling to Italy. It’s for the die hard risk-taking fashionistas that won’t step out of their house without a pair of heels. The ones that are a slave to fashion even when shopping for groceries. You know who your are. For everyone else, follow this guide on the best shoes for Italy.

The rumors are true. Italian women have a talent that sets them apart from everyone else: the ability to confidently walk in heels even over cobblestones.

If you really want to blend into the crowd on those hot, Italian summer nights, you need to master the art of walking in heels on cobblestone. While flats have a time and place, Saturday night at the discoteca in Positano is certainly not somewhere to bust out your best ballerinas. When it comes to walking in heels in Italy, even the mayor of Rome had something to say about the matter.

If you’re up for the challenge, here is my step-by-step instruction guide to help you overcome what is possibly the most dangerous thing for tourists in Italy. Try it at your own risk!


How to Survive Walking in Heels in Italy

Written by: Jasmine Mah


Pre-requisites: Please note that to even attempt this feat, you must be more than adequate at walking in heels when on home turf. If you only wear heels once a week for a few hours, I suggest you get extremely comfortable with them before coming to Italy. It would be better to wear flats and not fall on your face rather than wear heels and have a brutta figura (making a bad impression).


Choose one pair of shoes only as your “going-out shoes”




Why? You will probably have to throw them out at the end of the trip because no matter how careful you are, the heel will inevitably get stuck between the cobblestones at some point. Go with a heel height you are most comfortable with and aim to bring something with a slight platform at the ball of the foot as this always makes heels more bearable, increasing wear-time.

In terms of the style of the shoe, you will see Italians wear even the skinniest stiletto, however if it’s your first time, I suggest a stacked heel. What about wedges you ask? The fashion world is always split on whether wedges should be allowed to sit with the in-crowd but ever since Princess Kate was photographed wearing the Corkswoon wedge (by Stuart Weitzman), they’ve been gaining brownie points. You could definitely do a wedge in my opinion.


You need impeccable foot-eye coordination



Cobblestones are uneven and unpredictable, therefore, you need impeccable foot-eye coordination. Always look before you step, the worst face plants happen when someone gets too confident and forgets to look first.

Make sure to glance back up as well between steps, you can’t spend the entire night looking at the ground and risk missing the beautiful sights.



Walk lightly and put more weight on the ball of your foot



This helps prevent the heel from getting stuck in a crack and the further humiliation of having to pull it out with your hands after… Only transfer weight onto the heels if you’re on an even surface or have something to lean back on.


Grab a strutting buddy



This can be your travel partner, girlfriend, or better yet, grab a cute Italian boy. In the case that you feel unsteady or almost trip, your strutting buddy will provide support and hopefully catch you.


Take a break every now and then



There’s usually no reason that you should have to be running a marathon in heels or doing a long distance trek. Normally you might need to walk for a few blocks but then settle down at a bar for a round of aperitivo!



Always have blister bandages in your purse



I discovered the best ones (Elastoplast SOS Blisterplasters) after walking the Navigli district in Milan one night with a friend who developed the absolute worst blister I’ve ever seen. The pharmacist applied one of these (see photo) and it worked like a charm, we continued our night with no complaints. They are a lifesaver.



Remember, if you choose to wear heels in Italy save them for a special occasion not everyday sightseeing. Ultimately, when it comes to shoes and traveling, comfort always trumps fashion. Read this post to learn more about choosing the best shoes for travel. Happy strutting ladies! Ciao for now!

What are your best tips for walking in heels in Italy?  Share your comments below!


For more tips on travel shoes, please read:


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Author Bio: Jasmine is a pharmacist, foodie, and fashionista from Alberta, Canada living the sweet life in Bergamo, Italy. She currently curates all things fabulous and Italian on her blog Questa Dolce Vita and enjoys drinking wine in her spare time.