9 Chic Outfits to Elevate Your Italian Summer Vacation
There’s no place quite like Italy in the summertime. And while the sun-soaked coasts are must-visits, the cities are just as magical to make the centerpiece of your next getaway. Whether you’re strolling down the cobblestone streets of Rome or sipping an espresso in Florence, every scenario spent in Italy deserves a stylish ensemble. From great denim to elegant day dresses, what to wear in Italy this summer is made easy thanks to the street style scene, who, at last season’s Milan Fashion Week, showed up and out in arguably their chicest (and most recreatable!) looks yet.
When jetting off to Italy, pack pieces that are polished yet still practical. Lightweight, breathable silhouettes are ideal for navigating warm days spent seeing the sights–think flowy white dresses, oversized button-up shirts, slinky slip skirts, and more. According to one Milanese editor outside the Jil Sander fall/winter 2025 show, the latter looks especially chic accessorized with a sleek rope sandal and woven leather shoulder bag. Otherwise, continue to lean into elevated basics with a fashionable twist, such as colorful suiting, sheer midi skirts, and a raffia accessory (or two!). One attendee’s look captured this ethos perfectly by way of a sumptuous suede jacket (a city like Milan is known for having evenings on the cooler side) and a Miuccia Prada-approved boat shoe. Speaking of fabulous footwear finds, you’ll want to ensure you pack a heeled sandal for a festive night’s out, as well as a comfortable, yet chic pair of flats best suited for long hours on foot. You never know when aperitivo hour could be called!
Below, here’s what to wear in Italy–or really anywhere this summer–according to the street style scene. The gist? It’s all about effortless elegance with just a touch of trend.
A Sumptuous Suede Blazer With a Boat Shoe
Last season, no one could deny the suede blazer’s total fashion domination on and off the runways. This summer, the trend is back and better than ever with all eyes on this sumptuous collared jacket from COS. Styling-wise, take a cue from this Milanese darling and wear yours with a white denim mini skirt, a plain but perfect white tee, and a preppy pair of boat shoes. Summer-forward accessories, such as a woven leather handbag and pearl necklace, are a festive final touch.
A Boho Blouse With a Denim Bermuda Short
Thanks to Chemena Kamali at Chloé, the boho blouse continues to be the season’s hottest commodity. And clearly, this industry insider agrees. During Milan Fashion Week last September, she sported hers with a long-line denim Bermuda short and, for some welcome height, she slipped into a pair of heeled black sandals. The result? What to wear in Italy for daytime, as well as for elegant nights out.
A Flowy Slip Skirt With a Rope Sandal
Per this Milanese editor, styling a silky slip skirt with a crisp blue button-up achieves the ideal blend of structure and softness—and finished with a pair of woven rope sandals for that touch of Amalfi Coast charm. La dolce vita never looked so chic.
A LWD With a Colorful Summer Handbag
Elegant white dresses have made their mark on the spring runways as of late with brands like Bottega Veneta and Toteme standing behind the LWD. On your next Italian getaway, follow suit and slip into a breezy shirtdress with a colorful summer tote for that perfect pop of color. Not only does this chic combination work for casual daytime excursions but dressed up with a heeled sandal and sculptural jewelry, it’s perfect for a night out as well.
A Lace-Trimmed Slip Dress With a Mesh Ballet Flat
Navigate certain temperature changes in style by layering a lace-trimmed slip dress underneath a checkered, menswear-inspired blazer. Then, up the duo’s fashion game with a mesh ballet flat—preferably this coveted pair from Alaïa. Effortless layers and timeless textures—this is how the fashion crowd does vacation chic with a twist. Now, you too!
A Summertime Suit With a Festive Tote Bag
Take it from this industry insider: A pastel green suit brings fresh tailoring to the piazza, balanced by the delicate charm of crochet ballet flats. The finishing touch? A playful, festive handbag to match that dose of vacation whimsy—because bold color and confidence go hand in hand.
A Two-Toned Midi Dress With a Heeled Thong Sandal
A two-toned tank dress is a must-pack in your carry-on this summer—both modern and minimal—while heeled thong sandals add just the right amount of lift. Finish this look off like this showgoer with sleek silver jewelry and a chestnut-colored clutch.
A Preppy Cardigan With a Straw Basket Bag
Channel your inner Jane Birkin–yes, even in Italy–with a straw basket bag, an easy pair of blue denim, and a preppy cardigan. Whether you’re hopping a train to your next destination or perusing the shops, this look embodies that casual coolness we all strive for, whether on vacation or not.
A Crisp White Button-Up With a Sheer Midi Skirt
According to this chic attendee, mastering the art of masculine and feminine dressing is all about an oversized white button-up shirt paired with a sheer black midi skirt. Otherwise, turn to a structured leather handbag and some dainty jewels for even more subtle refinement. Wear this look straight from the sights to aperitivo hour. Andiamo!
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