All products are independently selected by our editors. If you buy something, we may earn an affiliate commission.
Planning a city break to Italy and want to blend in with the locals? Italian style is less about having a uniform and more about an in-the-know approach to fashion. Confidence is key. Consider well-fitting (not necessarily tailored), smart pieces such as a pencil skirt or a sleek knit dress, always freshly pressed and snag-free. Wardrobes here are bold but not flashy – one showstopper skirt can be paired with a simple knit, a style tip often seen on Mrs Prada.
For a more relaxed setting such as Tuscany, think of understated but always-chic brands such as Brunello Cucinelli and Loro Piana, or for a more attention-grabbing city look, look to Milan's big hitters – Fendi, Dolce, and Valentino – just a few of the names that put Italian fashion firmly on the map. When in doubt, follow this rule – dress from the shoes up. There’s a reason there are so many Italian shoe designers – Ferragamo, Tod’s, Sergio Rossi, as well as trend-leaders Miu Miu and Gucci. Well-made footwear is the mark of the well-heeled and is the foundation of any outfit. So whether you’re wearing a simple sandal or a va-va-voom stiletto, put your best foot forward and step into a new Italian wardrobe.
Amalfi Coast
This sliver of Italian coastline is known for its romantic, fairytale vista, so dress the part in pretty floral linens and sweet button-up cardigans, perfect for strolling through its cobblestone streets or stopping by a harbour town for ice cream. Pair with an embroidered straw basket to stock up on vintage finds and some non-flimsy ballet pumps. We love adding a touch of throwback charm with a romantic hair ribbon.
Rome
Italy’s capital is always smarter than the average European city; for a casual look that’s still polished, a statement midi skirt with a thin knit top is a great option for a day of sightseeing and cafe hopping. This look can be dressed up with a kitten heel for the evening or worn with a more fashion-forward shoe choice such as these playful penny loafers from Miu Miu - a nod to Rome’s coin-laden Trevi Fountain. Keep the overall outfit pulled together by opting for neutral tones or monochrome.
Milan
Not only is Milan seen as the fashion capital of Italy, it’s also arguably the fashion capital of the world. With the global glitterati flocking here twice a year for Milan Fashion Week, this is the city for full-throttle fashion: colour, print, pattern, and texture. A good way to keep things stylish is to look for classic pieces that pack a punch, such as a shirt dress in a bold hue, a la this geometric-print piece from La DoubleJ. Pair with long boots and colour-popping accessories such as an oversized hair clip or stylish sunglasses.
Tuscany
How to stay chic and stylish in the sun? The Italians have it nailed. Look for earthy, relaxed tailoring, such as a linen shirt set – updated for 2025 in sunset ochre or rust-hued red and worn oversized. Pair with a smart, open sandal, something that can keep you going through a vineyard tour or for cycling the hilly terrain, as well as a hat – we recommend a baseball cap for a Succession-meets-sporty take on sunshine dressing.
Sicily
One of the hottest holiday destinations right now, in no small part thanks to the likes of the second season of White Lotus, Sicily is the place for high-voltage holiday dressing, with looks to take you from beach club to after dark. Zimmermann is the go-to for bold yet sophisticated holiday dressing. This maxi dress is just as chic at the dinner table as it is by the pool. Pair with statement earrings and a simple sandal for a polished take on modern holiday dressing.
Venice
With its picturesque labyrinth of canals and bridges, its romantic heritage and world famous craft scene, it's no wonder that Venice is a bucket list destination for any traveller. Err on the side of formal when it comes to wardrobes as the city is more traditional that your average Italian getaway. We love a matching set that can be switched up – especially helpful for a hand luggage only weekend break – such as the below tapestry print skirt and top from Farm Rio. Be sure to pack a scarf to cover your shoulders for any religious buildings such as St Mark’s Basilica, and a wide brimmed hat to keep out of the sun for those all important gondola rides.
