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What to Wear in Italy

22 of Our Top Picks For Your Italian Holiday Wardrobe

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If you're planning an Italian getaway this summer, lucky you. Italy is one of our favourite countries in the world, filled with rich history, stunning topography, delicious food, and beautiful fashion. Whether you're spending time by the ocean, hiking and exploring the countryside, going through ancient ruins, or eating all the delicious pasta, there's never a shortage of fun activities. In short, you'll have an excellent trip. The only real difficulties you'll face are figuring out an acceptable time for your first gelato of the day — and deciding what to pack.

Whether you're exploring the canals of Venice, taking a dip in the water in Capri, or walking the countryside in Tuscany, you'll appreciate this roundup of what we'd bring to Italy this summer. It'll likely be hot, but it can occasionally cool down at night. You'll need easy sundresses, cool matching sets, comfortable shoes, and, of course a swimsuit or two. Plus, a quality crossbody is a must have for days spent adventuring and nights out. Keep reading to shop our selects, and save us some fresh foccacia!

A Statement Dress: We the Free Holy Smokes Maxi Dress

Feel like turning heads this summer? Put on this We the Free Holy Smokes Maxi Dress ($118) and get ready to be the star of the show. It can easily be dressed up or down, and versatility is key when travelling.

Image Source: freepeople.com
We the Free Holy Smokes Maxi Dress
$118
from freepeople.com
Buy Now

An Elevated Romper: Andrea Iyamah Shanti Romper

A romper is an ideal summer travel piece. It's great if you're spending the day walking through Rome or exploring coastal towns: it's comfortable to walk in and looks adorable. We love the tie waist on this cute Andrea Iyamah Shanti Romper ($250).

Image Source: shopbop.com
Andrea Iyamah Shanti Romper
$250
from shopbop.com
Buy Now

Denim Shorts: Levi's 501 Original High Rise Shorts

Denim shorts are a summer essential — you can wear them as a coverup or with a T-shirt and sweater for a more casual look. You can't go wrong with these Levi's 501 Original High Rise Shorts ($80). We love white denim for summer, but they also come in lots of blue washes.

Image Source: levi.com
Levi's 501 Original High Rise Shorts
$80
from levi.com
Buy Now

An Everyday Dress: Hill House Home The Daphne Dress

This Hill House Home The Daphne Dress ($150) is a new addition to the Nap Dress lineup, and it's gorgeous. It's a slightly more dressed up version of the beloved Ellie, with the same comfort we're used to. There's smocking in the back but not in the front, and it comes in this fun citrus print as well as a light-blue floral.

Image Source: hillhousehome.com
Hill House Home The Daphne Dress
$150
from hillhousehome.com
Buy Now

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A Reversible Bikini: Kya Swim Reversible Penelope Bikini Top and Kya Reversible Bikini Bottoms

Reversible bikinis are some of our favourites, because there's so much bang for your buck. The Kya Swim Reversible Penelope Bikini Top ($96) and Kya Reversible Bikini Bottoms ($82) are so sexy, and we love the classic silhouette. They have a fun, unique textured style on the flip side.

Image Source: freepeople.com
Kya Swim Reversible Penelope Bikini Top
$96
from freepeople.com
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Kya Reversible Bikini Bottoms
$82
from freepeople.com
Buy Now

A Black Dress: Endless Summer Inma Midi

Everyone needs a great black dress in their closet. This Endless Summer Inma Midi ($98) looks like a classic midi dress from the front. The open back, though, is perfect for summer days and nights.

Image Source: freepeople.com
Endless Summer Inma Midi
$98
from freepeople.com
Buy Now

A Crossbody Bag: H&M Shoulder Bag with Pouch

This H&M Shoulder Bag with Pouch ($25) is so affordable, you're practically required to buy it. We like that there are two straps: a chain-link shoulder strap and a thicker, removable crossbody strap. Plus, the little pouch attached to the crossbody strap is great for little things, such as keys or headphones.

Image Source: www2.hm.com
H&M Shoulder Bag with Pouch
$25
from www2.hm.com
Buy Now

A Casual Set: White Fox Boutique Golden Sunset Shorts and Behind the Look Shirt

These White Fox Boutique Golden Sunset Shorts ($40) and Behind the Look Shirt ($50) are the perfect casual day set for travelling. You can wear them to brunch, to the beach, or while shopping in the city. The shirt can be worn buttoned up or open with a tank or a bikini top underneath, and it also comes in white, blue, pink, and orange.

Image Source: whitefoxboutique.com
White Fox Boutique Golden Sunset Shorts
$40
from whitefoxboutique.com
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Behind the Look Shirt
$50
from whitefoxboutique.com
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A Strapless Dress: Caroline Constas Marnie Dress

Doesn't this Caroline Constas Marnie Dress ($480) just scream summer? It's the perfect brunch-to-beach dress, and you can even wear it out at night. Plus, it can be dressed up if you find yourself at a nice dinner.

Image Source: shopbop.com
Caroline Constas Marnie Dress
$480
from shopbop.com
Buy Now

A Bandeau Bikini: Stone Fox Swim Bijou Bikini Bottoms and Lele Bikini Top

These Stone Fox Swim Bijou Bikini Bottoms ($88) and the Lele Bikini Top ($88) make for such a sexy set. The bandeau bikini ensures minimal tan lines, and the double bottom side straps are so flattering. The set comes in a bunch of different colours, but we love this fun print.

Image Source: freepeople.com
Stone Fox Swim Bijou Bikini Bottoms
$88
from freepeople.com
Buy Now
Lele Bikini Top
$88
from freepeople.com
Buy Now

A Dress Under $50: Old Navy Waist-Defined Puff-Sleeve Cotton-Poplin Side-Cutout Mini Dress

Looking for an easy summer dress that's affordable and adorable? Pick up this comfortable navy Old Navy Waist-Defined Puff-Sleeve Cotton-Poplin Side-Cutout Mini Dress ($30, originally 35) before it inevitably sells out. It's easy to pack and will be comfortable for hot days in the city.

Image Source: oldnavy.gap.com
Old Navy Waist-Defined Puff-Sleeve Cotton-Poplin Side-Cutout Mini Dress
$30
from oldnavy.gap.com
Buy Now

A Straw Bag: Zara Woven Shopping Bag

A straw bag is the ultimate beach bag — sand won't get stuck in it. We like the long straps on this Zara Woven Shopping Bag ($50), which make it easy to carry. You can fit a book, aa snack, a bathing suit, and a small towel inside.

Image Source: zara.com
Zara Woven Shopping Bag
$50
from zara.com
Buy Now

A Dress With Pockets: Anthropologie Somerset Maxi Dress

This Anthropologie Somerset Maxi Dress ($168) is a great pick for summer exploring. It's elegant and elevated but still comfortable and easy. It comes in a ton of different patterns, and it even has pockets!

Image Source: anthropologie.com
Anthropologie Somerset Maxi Dress
$168
from anthropologie.com
Buy Now

A Comfortable Dress: Steve Madden Sleeveless Mini Dress

This Steve Madden Sleeveless Mini Dress ($49) might not look it, but it's actually supremely comfortable. It's made of a T-shirt material, so it's comfortable to wear every day, and the side ruching is super flattering. You can wear it as a beach coverup, out to lunch, or even to a party. At $49, it belongs in your suitcase.

Image Source: stevemadden.com
Steve Madden Sleeveless Mini Dress
$49
from stevemadden.com
Buy Now

A Ruched One-Piece Swimsuit: Gnash String One Piece Swimsuit

If you love a classic one-piece swimsuit, this Gnash String One Piece Swimsuit ($100) is the one for you. The side ruching is flattering, and we love the minimal straps and high-cut leg. It can also double as a bodysuit under jean shorts.

Image Source: freepeople.com
Gnash String One Piece Swimsuit
$100
from freepeople.com
Buy Now

A Day-to-Night Dress: En Saison Cavaretta Midi Dress

When travelling, you want at least one outfit you can dress up. This En Saison Cavaretta Midi Dress ($192) is it — it looks pretty with flats and heels and is supremely versatile. If a surprise party invitation presents itself, you'll know what to wear.

Image Source: shopbop.com
En Saison Cavaretta Midi Dress
$192
from shopbop.com
Buy Now

White Linen Pants: Free People Sky Rider Straight Leg Pants

If you like wearing pants, get something lightweight and comfortable. These white Free People Sky Rider Straight Leg Pants ($128) have large, super-functional pockets and a comfortable tie waist. We like them paired with strappy sandals and a white T-shirt or a button-down shirt.

Image Source: shopbop.com
Free People Sky Rider Straight Leg Pants
$128
from shopbop.com
Buy Now

Strappy Sandals: Staud Lara Espadrille Sandals

When it comes to footwear, versatility is key. These Staud Lara Espadrille Sandals ($350) are comfortable, have a little lift, and go with everything. They look great with linen pants or a bathing-suit coverup.

Image Source: shopbop.com
Staud Lara Espadrille Sandals
$350
from shopbop.com
Buy Now

A Linen Dress: Reformation Irwin Linen Dress

This white linen Reformation Irwin Linen Dress ($248) is a classic. The back is almost completely open, making the lightweight dress feel even breezier.

Image Source: thereformation.com
Reformation Irwin Linen Dress
$248
from thereformation.com
Buy Now

Cute Sunglasses: Karen Wazen Scarlett Sunglasses

If you're going anywhere in the summer, you need sunglasses. Give yourself the gift of these cool Karen Wazen Scarlett Sunglasses ($145). They have a retro shape that's dramatic and fun, and we love the tortoiseshell.

Image Source: shopbop.com
Karen Wazen Scarlett Sunglasses
$145
from shopbop.com
Buy Now

White Sneakers: Tretorn Nylite Plus Sneakers

Crisp white sneakers are another travel essential. These Tretorn Nylite Plus Sneakers ($75) are great for plane rides and days when you've got a lot of walking to do. Plus, they have a cushy inside with super-soft material, which will help prevent blisters.

Image Source: shopbop.com
Tretorn Nylite Plus Sneakers
$75
from shopbop.com
Buy Now

A Short Button-Down Dress: Hill House Home The Laura Dress

Going travelling this summer? Grab this gorgeous Hill House Home The Laura Dress ($165). It's versatile and comfortable, and we love the tie belt; you can tie it in the front or back. It comes in this lilac stripe as well as in black, a mosaic print, and a rose print.

Image Source: hillhousehome.com
Hill House Home The Laura Dress
$165
from hillhousehome.com
Buy Now

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