Here’s a fun story: I almost faceplanted at Lake Como because I wore flat sandals with zero grip 🤦🏻♀️
After many long trips to Italy, I’ve learned that Italy’s cobblestoned streets are unforgiving. Add the unpredictability of fall weather, and what you thought were the perfect vacation shoes can quickly turn into a hazard.
That near fall taught me the rule that now decides every shoe I pack for Italy: function and style have to be on the same page.
Here’s the thing about fall in Italy: it’s not one season. September is still summer, October is the transition, and November is when it finally happens. And the south, the center, and the north are all on different schedules.
So the right shoes for Italy in fall depend entirely on where you’re going and your exact dates.
This post breaks down 12 pairs by region and by month, so you can pick the 2 or 3 that match your exact trip.
Here’s what you’ll learn today:
✅ Exactly which shoes work in the south, central Italy, and the north, month by month from September through November
✅ The grip rule that saves you from the cobblestone wipeout I almost had
✅ How to mix and match just 2 or 3 pairs for your route, even if you’re visiting more than one region
Here are the 12 best shoes for Italy in fall, by region and month! (save it on Pinterest)
This post contains affiliate links. If you make a purchase through one of these links, I may earn a small commission at no extra cost to you. Thanks so much for supporting my blog if you’re planning to shop! 💛 (if not, just enjoy the post)
Estimated reading time: 15 minutes
The best shoes for Italy in fall are grippy, broken in, and matched to your region: sandals and sneakers cover the south all the way through November, central Italy adds loafers and waterproof sneakers by October, and the north calls for waterproof booties by November. Pack 2 or 3 pairs max, and check every sole for traction before it earns a spot in your carry-on.
🗺️ Jump to your region:
🍁 Central Italy (Rome, Florence, Tuscany)
🏔️ Northern Italy (Milan, Venice, the Lakes, Cinque Terre)
☀️ Southern Italy (Amalfi Coast, Sicily, Puglia)
Each region is broken down by month, because September, October, and November are three different trips in Italy. Find your region, then your dates, and your 2 or 3 pairs are waiting.
🍁 Central Italy: Rome, Florence, Tuscany
Central Italy is cobblestone country, and if your trip itinerary includes Tuscan hill towns, shoe regrets can happen.
Warm September days, drizzly October evenings, and a November chill. Your shoes for Central Italy in fall need to handle all of that. And don’t forget Rome’s sampietrini, the ancient hand-carved stones that get extremely slippery the second it rains.
You’ll also walk more here than anywhere else in Italy. Rome and Florence are easily 20,000 step cities. Comfort is not optional. But no worries, comfort AND style is my expertise!
😎 September in Central Italy:
Still summer shoes. Ballet flats dress things up without any bulk, and white leather sneakers handle the long sightseeing days.
For warm afternoons, add Arizona Eva / leather Birkenstocks or the VIVAIA walking sandals. One caution with both: smoother soles can get slippery on wet cobblestones, so save them for dry days and wear your sneakers if rain is in the forecast.
🌧️ October in Central Italy:
This is when rain enters the conversation. I experienced frequent drizzles in Bologna and Florence almost immediately after the calendar turned to October. The best walking shoes for Italy in October handle the damp weather without looking like rain gear.
Vessi Soho waterproof sneakers are exactly that: they look like regular sneakers, but your feet stay dry through surprise showers and puddled piazzas, so one pair replaces both sneakers and rain shoes in your carry-on. (this is the pair I’m traveling with this year)
Leather loafers are your second pair: polished enough for Florence dinners, flat enough to walk to them.
🎯 Also read: The best walking shoes for Europe!
☔️ November in Central Italy:
Bootie season begins. VIVAIA booties cover everyday walking with some polish, and the Vessi Soho sneakers stay in the rotation for wet days.
👠 Want a heel for dinner? Pashion convertible booties are the smartest way to do it: the heel comes off, so you walk flat all day and click the heel in at the restaurant. Just be realistic about cobblestones. Change into the heel when you arrive, not twenty minutes before.
🧳 Not sure how much to pack for Italy?
Shoes are only one piece of the puzzle. Answer 2 quick questions about your trip and I’ll send you a customized carry-on packing list, with the exact number of tops, bottoms, layers, and yes, shoes, for your dates.
Answer them here ⬇️
🏔️ Northern Italy: Milan, Venice, the Lakes
The north is the rainiest part of Italy in October and November, and Venice adds its own twist with acqua alta, the seasonal high water that floods the lowest streets. This is where waterproof shoes for Italy in fall go from nice to necessary.
One thing you don’t need: rain boots. They eat half a carry-on, and Venice is prepared for water in a way that will surprise you (raised walkways appear like magic). Waterproof shoes that look like regular shoes are the smarter play.
😎 September in the North:
No waterproof needed yet. Shoes for Italy in September up north are still summer shoes, so white leather sneakers are all the walking shoe you need.
Milan notices shoes, so add VIVAIA flats for a more considered daytime look, and leather Birkenstocks for the lakes and casual days. I packed these Birkenstocks for Northern Italy in September and October and was fine the whole time. If you do want a dressier look, then bring leather ones!
🍂 October in the North:
The rain starts, and this is Vessi Soho territory. Waterproof sneakers that don’t look waterproof are exactly what Venice in October asks for. I can tell you, I was so happy my Vessi Soho made it into my carry-on for my fall trip to Italy.
Pair them with leather loafers for dinners and dry days, and you’ve covered the whole north with two pairs. For real. 2 pairs!
☔️ November in the North:
Now it’s genuinely fall, so you’ll want to pack the best cold weather shoes.
Blondo waterproof booties are the workhorse: warm, dry, and polished enough for Milan. Your Vessi Soho sneakers handle the heavy rain days. I like to still have sneakers because I prefer not to wear boots (even though they’re necessary sometimes, I still try to avoid them 🤣)
And for dressy dinners, Pashion convertible booties pull the same trick here as in Florence: flat for the walk, heel for the table. Choose either the Blondo or Pashion bootie, both are great picks!
☀️ Southern Italy: Sicily, Amalfi Coast, Puglia
I personally love Southern Italy in the fall, because it refuses to admit summer is over.
September runs 75°F to 85°F (24°C to 29°C), October stays warm, and even November is mild. So shoes for Italy in fall look completely different down here: no boots, all three months.
I spent 6 weeks in Puglia and Sicily from late October through early December and was comfortably warm and dry until December hit.
That said, like everywhere in Italy, the south does have complicated terrain. Positano is basically one giant staircase, Sicilian hill towns are steep, and polished stones get slick. Down here, traction beats fashion every single time.
😎 September in the South:
Full sandal weather. My flat leather sandals are my daytime pick for flat coastal towns. If your itinerary is hilly, leave them home. This is the exact style that almost took me down at Lake Como.
For hills and stairs, my Italian leather platform sandals give you actual traction and enough height to work for dinner. They’re the pair I reach for when a town involves climbing.
Rounding it out: leather Birkenstocks (or Arizona Eva) for casual days, and VIVAIA all day walking sandals when you know you’ll be on your feet from breakfast to sunset.
💡 Pro tip: before any sandal goes in your bag, drag the sole across a smooth floor. If it slides easily at home, it will slide on wet Italian stone. That 5 second test is the whole grip rule.
😎 October in the South:
Still warm enough for sandals, honestly. The shift is that white leather sneakers become your main walking pair, with the VIVAIA sandals or these platform sandals from Quince covering warm afternoons and dinners out.
Two pairs. That’s genuinely all October in the south needs.
🧣November in the South:
Warmish, not cold. Boots would sit in your suitcase taking up space, and shoes are the bulkiest thing you pack.
Switch to closed toes: white sneakers for walking days (no need for waterproof) and leather loafers for dinners and dressier days.
💡 Pro tip: if you are planning to visit hill towns like Alberobello or Taormina at the end of November, into December, it will get cooler at night. These towns can get quite windy, and will definitely feel crisp. Booties are appropriate if you plan to spend significant time here and you’re also visiting the northern regions.
👟 How To Pick Your 2 or 3 Pairs
Here’s the part that makes this whole guide work: the right shoes for Italy in fall are simply the ones that show up in every cell of your trip. Find your region (or regions) above, find your month (or months), and the overlap IS your Italy packing list.
Rome and Venice in October? Vessi Soho sneakers plus loafers appear in both, so that’s your answer in two pairs. Amalfi in late September into Florence in October? White sneakers plus the VIVAIA sandals plus loafers, and you’re covered for sun, stairs, and cobblestones.
Three pairs is always my max, no matter how long the trip. I’ve packed for three months in a 20″ carry-on with three pairs, and I promise the fourth pair never earns its space.
🧮 Want to sanity check the rest of your bag? Run your trip through my carry-on packing calculator and it will tell you how many pieces actually fit for your dates.
Quick Recap: My Top 12 Shoes for Italy in Fall
- White Leather Sneakers. My personal pair, and they work in all three regions. (great if you don’t need waterproof shoes)
- Flat Leather Sandals. The ones I travel with, for flat southern towns.
- Italian Leather Platform Sandals. My personal pair, with the grip hilly towns demand.
- Leather Birkenstocks. The casual warm weather pair for September days.
- VIVAIA All Day Walking Sandals. Built for breakfast to sunset days on your feet.
- Ballet Flats. Zero bulk, and they dress up any September outfit.
- Leather Loafers. The polished flat that earns its spot everywhere.
- Vessi Soho Waterproof Sneakers. One pair replaces sneakers and rain shoes entirely. (only for rainy regions/months)
- VIVAIA Flats. The considered daytime flat Milan appreciates.
- VIVAIA Booties. November walking with polish in central Italy.
- Blondo Waterproof Booties. The warm, dry November workhorse up north.
- Pashion Convertible Booties. Flat for the walk, heel for the table.
And that’s how you cross Italy in the fall without a single blister (or faceplant).
Choosing shoes for Italy in fall really comes down to three questions: which region, which month, and does the sole have grip. Answer those and the 2 or 3 pairs practically pick themselves.
And whatever you pick, break them in before you fly. Italy is the wrong place to meet a brand new shoe.
Thanks for reading!
XO,
Aimara
PS: remember I can pack for Italy for you. For free, and yes, in a carry-on. Answer 2 quick questions here and I’ll send you a customized packing list for your trip.
About the author:
Hi, I’m Aimara, and I’ve been living out of a 20″ carry-on since 2021, traveling full time with my husband. We spent three months in Italy starting in September, moving from north to south as the season changed, so every shoe in this post was chosen with those cobblestones, stairs, and rainy Venice days in mind.
On Ways of Style I share packing strategies, capsule wardrobe ideas, and outfit inspiration for women who want to travel lighter without giving up their sense of style. Less stuff, more living.
MORE ITALY + EUROPE TRAVEL ARTICLES 👇🏼
- What to wear in Italy in September (by region)
- What to pack for Italy in October (by region)
- Avoid these 10 mistakes when packing for fall in Europe
- The best pants for Europe in the fall
- The 5 best shoes for travel (tested full time)
Shoes for Italy in Fall FAQ
What are the best shoes to wear in Italy in the fall?
The best shoes to wear in Italy are grippy, broken in, and matched to your region and month. In September that means sandals, sneakers, and flats almost everywhere. By November it means sneakers and loafers in the south, and waterproof booties in central and northern Italy.
Can I wear sandals in Italy in October?
In the south, yes. Sicily, the Amalfi Coast, and Puglia stay warm enough for sandals well into October. In central and northern Italy, October is sneaker and loafer weather, and sandals only make sense on the warmest early October days.
Do I need waterproof shoes for Italy in the fall?
In central and northern Italy from October onward, yes. October and November are the rainy months, and Venice can flood with acqua alta. Waterproof sneakers are the best shoes for Italy in fall rain because they replace both your sneakers and your rain shoes in one pair.
Are white sneakers OK to wear in Italy?
Yes, as long as they’re clean leather sneakers rather than bulky athletic shoes. Italians wear leather sneakers everywhere, and they’re the single most versatile pair you can pack: they work in all three regions, all three months.
Can I wear heels in Italy in the fall?
Thin heels and cobblestones are not friends, so I skip traditional heels entirely. If you want height for dinner, convertible booties with a removable heel let you walk flat and click the heel in at the restaurant, which is the only version of heels I recommend for Italy. Booties also look great when worn with my favorite fall travel dresses!
What shoes should I wear in Rome in the fall?
Rome is 20,000 step days on cobblestones, so grip and comfort come first. In September and October, clean white leather sneakers and loafers are ideal. By November, add a pair of waterproof sneakers for rainy days. Skip thin heels entirely, since the sampietrini stones will swallow them.
What shoes should I wear in Florence in the fall?
Florence dresses up at night, so pack for both the walking and the dinners. Leather sneakers and loafers handle the daytime galleries and cobblestones, and convertible booties with a removable heel let you go dressy for dinner without carrying a second pair. Change into the heel once you reach the restaurant, not before.
What shoes should I wear in Venice in the fall?
Waterproof, every time. October and November bring rain and acqua alta, the seasonal high water that floods the lowest streets. Waterproof sneakers keep your feet dry and still look like normal shoes, which makes them the best walking shoes for Italy’s wettest city. Leave the rain boots at home, since Venice sets up raised walkways when the water rises.
How many shoes should I pack for Italy?
Two or three pairs, never more. When you’re deciding which shoes to pack for Italy, match your region and month first, then pick the pairs that overlap across your whole route. I’ve traveled Italy for three months with three pairs in a 20″ carry-on, and the fourth pair never earns its space.
DID YOU LIKE THIS POST ABOUT THE BEST SHOES FOR ITALY IN FALL? SAVE IT FOR LATER OR SHARE IT WITH A FRIEND! 📌
Leave a Reply