Italian Style with Travel Italian Style!

In preparation for my upcoming vacation to Italy, I reached out to our AMAZING new friend and travel planner Cassandra Santoro who owns the uber successful blog and Italian travel planning company appropriately named Travel Italian Style. Read along below for a wealth of info from her and style tips and links from us interspersed throughout!

Dressing with Italian Style
By Cassandra Santoro

These are a few of the Looks & Merit style picks based on Cassandra's excellent advice. You'll find links to these items and a few more throughout her blog post!

These are a few of the Looks & Merit style picks based on Cassandra's excellent advice. You'll find links to these items and a few more throughout her blog post!

I have spent ten years living back and forth between Florence, Italy and New York. During this time I found myself desperately trying to immerse myself in the Italian life. Even as a Sicilian-American with a dual citizenship, being an Italian tour guide, running my own Italian travel company, and even almost marrying a Napolitano man, there was one thing I could never fully figure out and this was how to dress with Italian Style.

It wasn't until one day my business partner said to me "Cassie, it’s easy, the TRUE Italian Style is simple. Simple is the real class, simple is Italian style. "

It took me a day to fully absorb what had been shared with me but then suddenly it hit me. It was that day that I stopped questioning my outfits and went back to my roots. Soon enough I was able to walk with confidence on the streets of Bella Italia.

How did I do it? Well, I stopped over thinking and kept the focus on the simplicity of the Italian lifestyle.

The truth behind the truth

Italians give the impression that they are always 'dressed to the nines', but that is not always the case. They are just smart about it and you should be too.

Let’s start with the basics. Did you know it’s common to wear the same shirt two days in a row? In Italy, you can actually get away with wearing the same shirt twice in a week without a second glance.

A nice jacket, a scarf, or adding a layer shirt can give you a whole new look! Just add one unique addition to your already put together outfit, and ecco, you have a new style! Remember, accessorize but do not overdo it—keep my earlier advice in mind, classy and simple.


  1. Scarves: Gorgeous orange printed fruit bandana (from the above graphic), a classic blush and black silk tulip-print stunner, this delicate floral square silk scarf in teal, and a fun cotton lemon-print bandana.
  2. Jackets: Try a powder pink leather jacket with fun but classic moto detailing, this washed leather leather jacket in always-appropriate black (I own it in the cabernet color and can vouch for the amazing fit) or a fail-proof chunky textured cardigan in a neutral hue for chilly museums or breezy evenings.
  3. Layering Pieces: This printed poncho has enough grey to keep it neutral yet a little fun pop of color on the border and the Madewell cape scarves are incredibly versatile and stylish travel companions - the armholes are brilliant!


However, I am not saying there are not times where maybe you may want to step up your style game a bit. If you are traveling from North to South of Italy during one trip, you may notice Milanese are a bit more designer focused than the Southern Italians (for example). Or there are certain fabrics and accessories that you find on the Amalfi Coast that you will not see in Florence. Just like anywhere, each region has its own flare.

With that being said, I thought it would important that I also shared a quick run down of simple tricks for each region, so you can walk with confidence no matter where you are traveling in Italy.

The Lakes + Northern Italy

As you may already know, Milan is the fashion capital of Italy. In addition, it is also important to remember that Lake Como is just a hop, skip, and a jump away from the city center. The Lakes hold the keys to homes of the likes of George Clooney, so it’s natural you may feel a bit more inclined to step up your fashion game while touring in this region.

While touring the North try a staple piece such as a fitted dress, straight leg jean and a blazer. Then add a silk scarf (silk is well known up north), a big fancy hat, or your favorite heeled shoe (I am a fan of a nude color) and you will be set. Sure you may want to add a red lipstick or an accessory with a pop of color but when in doubt choose a neutral shade.

Florence + Tuscany

Florentine and Tuscans are well immersed in the fashion world as well. As the home of Pitti Immagine events, they always look their best. However, despite the Italian stereotype of women, an average day in the city center of Florence does not always mean you must rock your stilettos on these cobblestone Renaissance streets.

While locals are in tune with current trends, it is common to find an everyday look to be complete with a scarf, a locally made leather jacket, and great sneakers or even comfortable but stylish flat shoes (we love these cream pointed-toe mules).

I am not saying you will not find many with designer bags and pumps. This is after all the region of the infamous Ferragamo family. (Our favorite Ferragamo bag for travel is the Ginny Medium Shoulder Bag in red saffiano leather - find it here!)

However, not everyone can afford a designer look, so many times Italians invest in that one piece that makes them not only feel confident but that is also practical for all occasions. For me, a fitted leather jacket is a secret. Florence is the home of leather, so you can get a custom made piece at a great price. Plus it is perfect for all seasons and flattering on all body shapes!

Quick Tip: Why not try Benheart in the city center of Florence for a fabulous custom made leather bag, jacket, or shoes!

Amalfi Coast + the South

The Amalfi Coast is everything you dreamed it would be: blue waters, white lines, and handmade leather sandals.

On the beach, the trend is easy to spot: less is better (for men and women). However, when strolling the town be sure to have a great pair of strappy sandals or wedges and leave those flip flops for the boat and beach only! Whether you spend 5 Euro or 200 euro these scarpe are still only for the sea days. 

What to wear off the beach? I say choose a fitted, simple, sexy, and (you guessed it) classy look.

High wasted ripped shorts aren't common around these parts. You will most likely feel more comfortable with a wrap dress, a beautiful pair of sunglasses (our favorite statement-making cat eye sunnies, pictured above, are from Krewe and Le Specs) and a bright statement beach bag.

You will also notice in the south many boutique shops offer locally made beach cover up’s. While many locals and tourists in the region flaunt these handmade beauties, my advice is to consider a simpler look.

Feel free to make the purchase during your visit but, from experience, I found a plain style or even a white ‘flowy’ dress has been the best investment. 

It's easy to be drawn to the colors and beads, just keep in mind practicality before making the purchase. Can you really see yourself using this cover up again outside the dreamy beaches of Positano?


  1. Dresses: This easy breezy white bell-sleeved dress (pictured in the graphic, above) is comfortable enough to sightsee in all day and dressy enough to transition into dinner at night with fun accessories. This strappy utility midi dress (also pictured above) comes in a flattering olive hue and is another beautiful yet comfortable item that will work strolling around Rome and by the beaches in Amalfi. And as if places like the coast of Capri couldn't be more picture perfect, this blue and white embroidered dress is picture-worthy in and of itself. Last but certainly not least, this Tory Burch wrap dress would be a beautiful addition to your wardrobe for your vacation and beyond!
  2. Sandals: I've mentioned these Cole Haan lace-up beauties (pictured above) a few times before, but they truly are the most stylish and most insanely comfortable sandal I own!
  3. Style essentials: A simple white details can go a LONG way, and the perforated details and dolphin hem of this one will allow you to style it multitude of ways like under a blazer, belted over a midi skirt or over skinny trousers with a bright scarf. Another white top that will work overtime on your trip, from day to night, is this one-shoulder ruffle top from Madewell. 


Are those really all of my secrets? I am not a style guru but I have been taught to look at Italian style like a local. Not everyone lives like its fashion week in Italy, instead, they encourage what they know and that is, always, less is more, use what you have and walk with a smile and no one will doubt your look.

Recap of how to dress with confidence in Italy

·      Stay focused on what makes you feel great

·      Add a few accessories or layers to your already purchased staple pieces

·      Make a few traditional and local purchases to spruce up your look

·      Smile

Keep these tips in mind and you too can be completely immersed in the la dolce vita lifestyle of any European country you may be traveling.

Ci vediamo in Italia

About Cassandra:


Cassandra Santoro is the CEO and Founder of Travel Italian Style. As a personal trip planner, Cassandra is an expert in Italian travel with a focus on authentic and inspiring experiences. She also leads motivational talks and can most recently be found at TEDx DHBW Mannheim. Cassandra is currently writing her first series of short stories and lives between NY & the South of Italy. Follow her adventures in Italy on Instagram.

Hannah Benak