What To Wear In Italy This Fall: Venice, Florence, Rome 12 Italy Outfit Ideas To Wear This Fall
Not sure what to wear during your October trip to Italy? Although it’s technically “fall” in October, Italy remains in the seventies-low eighties with mostly sunshine.
I lived in Florence for five months in 2022 so I knew exactly what to pack for my ten-day trip to Italy this fall. Think easy maxi dresses, lightweight linens, a few layering pieces, and whatever shoes you’re most comfortable in.
Today I’m sharing all twelve outfits I wore during my trip to Venice, Florence, and Rome complete with links to shop and directions to each of these iconic photo locations so that you can recreate these pictures for your own Instagram.
Enjoy!
Gondola Riding
You can truly wear whatever when riding a gondola but if you have a favorite dress you’ve been saving, now is the time to pull it out. This is probably one of the most romantic + best photo ops you’ll have throughout your time in Italy so wear whatever you feel best in.
I had been saving this stunning red dress and it was perfect for these Instagram photos + evening dinner and drinks. Fancier than what the average person is wearing in Italy but so good, haha.
photo location ✈ Canal Grande, Venice
Walking Tour Of The City
The key to acing your outfits in Italy is bringing something trendy yet functional. I knew this puff sleeve maxi dress would be perfect (shoulders and knees covered in case we went to any churches) and 100% cotton so very breathable for the eighty-degree temps!
Highly suggest packing whatever shoes you feel best in. Most people call me crazy when they find out I do Europe in sandals but I have flat feet so 0 support shoes tend to be just fine for me. I packed four pairs of my tried and true favorites that I knew would leave me with zero blisters — that’s key!
dress || sandals || clutch || sunglasses
photo location ✈ Rio dei Fuseri, Venice
Foodie Approved
Every Euro girl is wearing a denim maxi skirt right now. They are the perfect summer-to-fall transition piece and are so easy to style. I ended up wearing this for an afternoon in Florence with a stunning corset and then again in London layered with a long-sleeved bodysuit and scarf. Such a versatile piece to pack if you’re headed places afterward!
Wanted to give these shoes a special shoutout too—I’m a firm believer that certain outfits just need a pair of lace-up shoes. Italy certainly isn’t suited for my favorite heels so I ended up bringing these Dolce Vita shoes instead. They have a one-inch heel so they are sort of like sandals sort of heels and they are real leather so once you break them in, very bearable for a few miles of walking! I styled them a ton throughout this trip with some of my dressier pieces.
photo location ✈ Ponte Vecchio, Florence
Aperol O’Clock
You know that one outfit that you’re more excited to wear than any of the other things you brought?! This ombre maxi was mine! The day I saw this on Petal & Pup’s website I knew it would be perfect for happy hour in Florence with a matching Aperol spritz in hand.
I can’t even count how many strangers stopped me on the streets to compliment me on this. It was a huge hit!
photo location ✈ View on Art Rooftop
City Chic
I felt so sexy in this black two-piece set from Shein of all places! This mock neck top and mermaid skirt combo is perfect for exploring the city—whether you’re visiting a church, grabbing drinks with friends, or watching the sunset from Piazza Michelangelo you’ll look effortlessly chic in this number.
Becuase it’s silk it automatically had a dressier feel to it. I tried dressing it down with a simple gold sandal, claw clip, and sunnies!
set || sandals || sunglasses || purse
photo location ✈ Santa Maria Del Fiore, Florence
Weekending At The Winery
You can’t go to Italy without taking a trip to the Tuscan countryside. This area is home to all the best wineries aka the perfect spot to pull out your best dress! This stunning silk strapless dress went so viral on my Instagram! Rightfully so… this cowl-back dress is so flattering, hugging every curve so effortlessly.
Definitely one of my favorite outfits of the trip!
photo location ✈ Castellina in Chianti
Linen Lover
You’ll be walking a minimum of 15,000 steps a day when exploring Italy so wearing something you’re both cool and comfy in is key. For me, that means all the linen dresses. If I had another one, I packed it haha. Specifically, maxis to give things a little more of a fall feel! I love the strappy cutouts along the mid-drift and the open-back detail of this one. So cute!
dress || sandals || tote || sunglasses
photo location ✈ All Antico Vineo, Florence
An Evening In Roma
You can never go wrong with a little black dress… even in the middle of October in Roma! I styled this dress in white on one of my beach vacations this summer and loved it so much that I grabbed it in black to bring to Italy! Plunging neckline without being tii booby + an open back that’s too cute.
I paired this with ballet flats…. well, just for the picture. I legit couldn’t walk in these for more than five minutes without getting blisters. But if I packed them, you better your a$$ I’m at least getting a photo in them, lol.
dress || purse || sunglasses || flats
photo location ✈ Trevi Fountain, Rome
Playing Tourist
Nothing screams Italy like a corset dress. This style originated in Venice so it’s super fitting to pull out this classic shilouette during your trip here! I saved this cotton tank dress for our hottest day and was so glad I did.
For an elevated, Pinterst-approved look go for matching sandals + sunglasses then tie a sweater around the shoulders.
dress || sweater || sunglasses || sandals || purse
photo location ✈ Colosseum, Rome
Sunday Strolling
Another linen dress… who’s shocked?! This white one was one of my favorites of the trip! This was another Commense find and it did not disappoint. Double-lined throughout the cups so you can go braless and it has a deep open back that’s sexy without trying.
This was a little longer, hitting right at the ankles so I kept things super simple with my favorite Dolce Vita sandals. I have these in three colors and they are hands down some of my most comfortable leather shoes. No blisters ever!
dress || sandals || purse || sunglasses
photo location ✈ Mimi E Coco, Rome
An Evening In Venice
Both this tank top and skirt were last-minute additions to my suitcase and I’m so glad I ended up bringing them with me. Styled together, this was the cutest combination for an evening out in Venice. I wore this to dinner which quickly turned into 2:00 am rooftop drinks… oops!
Lots of questions on this tank. It is sheer but I have these nipple covers on with it. I wore this skirt two other times on this trip— once for an evening walking tour with sneakers, and again with a lace tank to the bars so needless to say this was a must-pack item for me!
tank || skirt || sandals || purse
photo location ✈ Cinema Italia, Venice
Sight Seeing Approved
I didn’t get a great photo in this dress but wanted to include this outfit regardless since this was a great affordable (under $25) option to buy for your Italy trip. I wore this for a walking tour in Florence one morning and it was the perfect comfy, casual attire.
If you’re someone who struggles with putting outfits together a dress could be your best friend! Just add sandals and accessories and you’re ready to hit the town with no time wasted!
dress || purse || sunglasses || sandals
photo location ✈ near Hotel Unicorno
Still wanting more Italy outfit ideas? I shared an Outfits Of The Week post every week I lived in Florence so I’ve got plenty of looks to go around—click here to browse through those archives.
It was a magical feeling being back in Italy + we truly came at the perfect time. The first week of October is known to have some of the best weather of the year. No goosebumps and no sweating which is considered two wins in my book, haha.
Our next stop is Copenhagen, Denmark the rising fashion capital of the world… stay tuned!
xx
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