10 Chic Outfits to Wear While Exploring Sicily

With its sun-soaked streets, ancient ruins and vibrant culture, Sicily has a charm that is impossible to resist.

When I visited and explored the island back then, I wanted outfits that embodied its effortless elegance while keeping comfort in mind.

Every day really was like going onto a movie set, and the part of the adventure was getting dressed up.

This guide will show you how to pack chic outfits that are comfortable enough for all-day sightseeing, but look good enough for those Instagram-ready moments.

From seaside villages to ancient sites, here’s how to do Sicily in style.

1. Flowy Midi Dress

A light midi dress is perfect for Sicily’s warm weather and lovely scenery.

Accessorize it with flat sandals for leisurely daytime walks through cobblestone streets, or tour of a winery.

So easy, in fact, to accessorize mine with a pair of statement earrings for a nice dinner.

The lightweight materials keep you cool while still looking polished and sophisticated.

2. Pants and Button-Down Shirt in Linen

Linen is airy and stylish, ideal for those sunny Sicily days.

I wore neutral-toned linen pants with a nice white button-down shirt, and I was comfortable all day.

Roll the sleeves and throw on espadrilles for a casual mood, or tuck it in and add some accessories for a dressier combo.

It’s a flexible getup well-suited to market stops and al fresco cafés.

3. Sundress with a Wide-Brim Hat

A sundress and hat combo is a classic option for exploring Sicily’s coastal towns.

I enjoyed wearing mine while strolling around Marzamemi, where the colorful streets seemed like a natural fit.

Flat sandals or espadrilles finish the look, and the hat serves double duty as sun protection for long days out.Fully equipped, even for long days outdoors.

It’s a classic, uncomplicated outfit that can never go out of style.

4. High-Waisted Shorts and a Cropped Top

For casual exploring, a pair of high-waisted shorts with a cute, cool crop top that’s stylish but practical.

This was my hiking outfit while I was near Mount Etna — it was lightweight but still easy to move in.

Throw on a crossbody bag and sneakers, and you’re set for everything from historic sites to nature trails.

The combination of casual and trendy is a go-to look.

5. Wrap Dress

A wrap dress has many uses and is flattering, ideal for game of Sicily’s romantic game.

Wear it, during the day, with a comfy pair of sandals for walking tours, or for visits to churches.

For evening, switch out the sandals for block heels, and add a clutch for dinner by the sea.

It’s a look that slides from day to night, all while being effortlessly chic.

6. Palazzo Pants and Tank Top

Palazzo pants are stylish and cozy, ideal for the Mediterranean energy in Sicily.

I wore my with a plain tank top and flat sandals for a relaxed but chic aesthetic.

A light scarf adds a pop of color, and can be used to cover your shoulders when entering holy sites.

I think this outfit was ideal to explore cities like Noto where style and comfort can be worn together.

7. Denim skirt and off the shoulder blouse

The denim skirt lends a casual touch, and the off-shoulder blouse adds a hint of romance.

I wore this look in Ortigia, and it felt fun but still polished.

Pair with espadrilles and a woven bag to set a casual, Mediterranean mood.

It’s an excellent choice for warm afternoons by the sea or wandering historic town squares.

8. Maxi Skirt and Tank Top

A floaty maxi can’t help but fit the laid-back appeal and theatrical vistas of Sicily.

Balance it out with a fitted tank top and, for comfort, flat sandals or sneakers.

So this ensemble – for a day at the Valley of the Temples, too, where I wanted something stylish but also practical – worked a dream.

It also gives your style a glam flair (the movement of the skirt is a nice touch for photos!).

9. Jumpsuit

The ultimate in one-and-done outfits, jumpsuits are perfect for travel days or long excursions.

I picked a linen jumpsuit for its breathable fabric and chic silhouette, and it made a world of difference.

Wear it with sneakers or sandals by day, then finish with a belt and heels at night.

It’s functional, trendy, and barely takes up any real estate in your suitcase.

10. Little White Dress

A little white dress is a summer essential, and has a particular resonance for Sicily’s sun-kissed streets.

I wore mine while walking the streets of Cefalù, and it looked just right against the beach and old town.

Style with tan sandals and a straw bag for a classic Mediterranean feel.

It’s a multiuse item that goes for everything from the sightseeing to sunset dinners.