There’s no question that my favorite region of Italy is Sicily. I often joke that Sicily is what Americans are really looking for when they head to Italy. The Sicilian hospitality, the sultry drama of baroque cities, the melodic Sicilian accents, the food! Whenever there’s an opportunity to head to the Mediterranean island, I jump at the chance, carry-on ready.
I have mastered packing my carry-on for a weekend in Sicily, having learned from my many trips to the island and observing what I needed and what I actually wore. From elevated swimsuit cover-ups and stylish sandals to breezy dresses and jumpsuits, here are my wardrobe must-haves for a holiday in Sicily that work every time.
Sicily Wardrobe Essentials
Cotton Poplin Dress
Nordstrom
One day, while visiting Ortigia in August, my husband and I stopped at a famed sandwich shop. It was a long line, and the sandwich maker pulled me out of line, calling me a “regal queen,” and let me get behind the counter to take photos with him. I’d like to think this was in part due to my dress.
It was a white cotton poplin Tory Burch dress in a timeless 1940s-style silhouette. With the breezy poplin material, I wasn’t melting in the Sicilian morning heat—or at least I didn’t look it. This white Staud halter dress with a dramatic bow back is loose and airy, perfect for those early mornings or late afternoons under the hot Sicilian sun. This Rag & Bone poplin dress is a similar shape to my Tory Burch dress—elegant and structured, but not clinging to your body.
Linen Button-bown
Quince
On advice from Italian designer Stella Jean, an essential for Italian summer style is the slightly crumpled linen button-down. Throw it over a swimsuit or with a pair of linen trousers. A linen shirt works overtime on a Sicilian holiday, and I adore this 100-percent European linen style from Quince that rings in under $50.
Versatile Shorts Set
ShopBop
ShopBop
From an easy, no-brainer breakfast look to wandering around all day, a matching short set is the perfect blend of comfort and polish. I especially love the effortless vibe of pairing shorts with a button-down—ideal over a swimsuit for going straight from the beach to a lunch table. Worn together, the set feels chic and put-together; worn separately, each piece holds its own.
This Farm Rio version, with its vibrant scenes reminiscent of Sicilian churches, ceramics, and seaside views (though the brand itself draws inspiration from Latin America), makes a bold yet breezy statement. Crafted in a linen weave, it’s comfortable, travel-friendly, and—bonus—has pockets included.
(Actually) Stylish Water Shoes
Zappos
Hopping on and off a boat or sipping an aperitivo near the Marsala salt flats? I have to admit, I’ve ruined more than a few leather sandals seaside. That’s why I love that chic jelly sandals—like this pair from Sam Edelman—are back on trend. They’re the ultimate vacation flat.
Flowy Kaftan
ShopBop
You’re in Sicily—so lean into the drama! Channel Sophia Loren’s holiday glamour with this one-shoulder Diarrablu kaftan dress. Effortless to pack, this flowy statement piece captures the essence of Italian nonchalance. Just add one bold accessory—whether a bracelet or a striking earring—for an easy, breezy take on Sicilian glam.
Breezy Jumpsuit
Anthropologie
Along the same lines as the glamorous ease of the kaftan is a bold, printed jumpsuit. There’s something about this look that always turns heads. The wide-legged style of this Anthropologie jumpsuit makes it beautiful on a variety of body types, and a strappy sandal, flat, or block heel takes it straight from aperitivo to dinner.
Bold Printed Dress
Nordstrom
Bold, beautiful prints and fit-and-flare silhouettes are quintessentially Sicilian—some Italian brands have built entire empires on this aesthetic. I always pack at least one printed dress for Italy; it’s my go-to for evenings out, paired with a low block heel. For a trip to Sicily, you’ll want the same. This Maggy London palm-print dress is flattering, lightweight, and perfectly channels the island’s sun-soaked energy.
All-terrain Sandals
Zappos
Whether it’s hiking into a cove in Vendicari’s nature reserve or a 40-minute path down a canyon into the emerald waters of a lagoon at the Cavagrande del Cassibile nature reserve, some of the most beautiful bits of nature in Sicily are a bit of a hike to get to. There were several occasions where I was thrilled to have worn my sturdy Tevas instead of flip-flops. Sometimes the most beautiful views are absolutely worth it. I love the all-terrain sole of the Hurricane Xlt2s, and I’ve never regretted bringing them on an island adventure.
Elevated Cover-up
Amazon
I love scouring sales and vintage stores for timeless Missoni trousers like these at Net-A-Porter. Bold jewelry, Missoni zig-zags, and a beachfront backdrop—it’s so la dolce vita. When heading to Sicily, I pack one or two pairs of Missoni trousers, instantly elevating my loungewear style. For a similar vibe, this Amazon two-piece set offers that same luxe ease—comfortable, effortless, and perfect as an elevated beach cover-up.
Wide-brim Sun Hat
Amazon
The Sicilian sun is hot! And if you’re going to be wandering around exploring in the midday sun, be sure to wear a sun hat. A simple baseball cap doesn’t offer enough coverage. Get a wide-brimmed hat that’s stylish and practical. Lean into the retro vibes of film stars of the past with this extra-wide-brimmed sun hat. Remember, the term ‘paparazzi’ was created in Italy. With this hat and your sunglasses below, you might be dodging the paparazzi on your Sicilian holiday.
Stylish Tote for Local Groceries
Gap
Yes, the fresh produce in Sicily is as delicious as they say. While driving to the beach, we often pull off to a roadside farmstand and get our snacks for the day, like delicious cherry tomatoes washed in seawater. You’ll definitely be doing a lot of local shopping, so bring a stylish tote that doubles as a grocery bag, like this slouchy raffia bag from Gap.
Sleek Water Bottle
Amazon
It’s going to get hot! On days spent exploring Sicilian towns, you should have a great water bottle in tow that keeps your water ice-cold all day. Instead of countless trips to the supermarket to fill up your bottle or long tabs at beach clubs, bring a reusable water bottle with you and fill it up at public fountains.
Cool Sunglasses
Amazon
In Italy, sunglasses are the must-have accessory. Treat yourself to a pair to last from vacation and beyond. My go-to pair is these foldable Ray-Ban Wayfarers. A classic cool shape, this foldable style is perfect for travel as it easily fits in a purse or pocket. While I love a bold pair of sunglasses with all of the flourishes, the lightweight, sleek design of these Wayfarers doesn’t weigh on your face on those hot, sunny days.
Silk Hair Wrap
Amazon
I love my velvet head wrap with tassels from headware artist Julia Clancey, and I wore it a few times in Sicily before it was too hot. Velvet, while gorgeous and luxe, isn’t the best for Sicilian summers. Here’s a lightweight, pre-made hair wrap in 100-percent silk from the brand Silke London. Sure, you can use it for sleeping, but this elegant option can keep your tresses smooth on an airplane, at bedtime, and is simply a stylish choice for post-beach hair in the Sicilian evenings.
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