How to Dress Like an Italian: Fall and Winter Edition

Fashion in Italy is serious business – so it’s no surprise that lots of travelers often ask us how to dress like an Italian while they’re here! While you certainly don’t have to dress like a local when you’re visiting, and while you should definitely wear what you’re comfortable in, immersing yourself in the culture can be part of the fun. And that means dressing (and shopping!) like the locals do.

In the fall and winter, the Italian dress code entails bundling up with lots of layers. In fact, one thing foreigners often comment on is how Italians often start wearing heavier clothing around October, regardless of whether the weather’s actually still quite warm and mild… simply because it’s time for the cambio di stagione (change of seasons)!

When dressing for the weather, remember that the climate varies depending on where you’re going. It’ll be relatively mild in Naples and the south, getting colder as you head north—and it’s often downright bone-chilling in the dead of winter in Milan.

Here are our top tips for effortlessly chic Italian style for both men and women in the colder months. And for the most up-to-date Italian fashions, don’t forget to check out our Italian style page on Pinterest!

(Coming in the spring instead? Here’s our guide to Italian fashion in spring!).

Pile on the neutral colors

Jeans and a sweater is a great casual, but fashionable, look

Classic neutrals like black, gray, brown and camel pop up more than usual in the colder months; you’ll also see Italians using these neutrals as a background for a “pop” of a bolder, darker color, like burgundy or forest green.

Meanwhile, the “no white after Labor Day” rule in Italy doesn’t exist: Locals love winter white, especially for jeans and sweaters.

Jeans can be chic – but colored pants are also popular

In Italy, jeans are popular. They’re considered a bit on the casual side, but as elsewhere, a beautifully-fitting pair of jeans can always be dressed up with great boots or heels, a nice blouse, and layered jewelry, which is a combination you’ll see on many Italian women.

Men, too, wear jeans, although it’s generally seen as a more informal way to dress, and not something you’ll see most men wearing while they’re out to a nice dinner or elegant drinks.

As much as you’ll see blue and grey denim washes in Italy, you’ll also see lots of colors. Colored trousers remain popular throughout the fall and winter months, with colors ranging from dark green to taupe.

Don’t leave home without your sunglasses

That’s right: Sunglasses are all the rage, even in the winter! Italians don’t leave home without a pair of stylish pair of large, dark sunglasses, a great way to pull any outfit together… and add a level of glamorous mystery.

Think timeless outerwear: a trench or blazer when the weather’s warmer, a classic overcoat when it cools down

Stylish men in the streets of Florence. Photo by TRÈS BIEN (Flickr)

When the weather’s crisp, but not freezing, try out a timeless trench coat, blazer or khaki jacket. (Tailoring always is key!). As the temperatures dip more, pack a slim-cut tailored overcoat (Italians can be spotted in both single- and double-breasted coats); a more recent trend has been a down jacket with a fur-lined hood, a great way to keep toasty when it’s freezing!

Classic jackets on a rainy day in Venice. Photo by Robert Trm (Flickr)

Don’t go anywhere without your leather or suede boots (or booties)

The perfect winter Italian look: a slim-fit jacket, hat, colored pants and booties (Photo: Nicoletta Reggio of the Italian fashion blog Scent of Obsession).

Italian women love their sky-high heels… but we understand that not everyone walks gracefully in them on cobblestoned streets! To blend in without sacrificing comfort, look for leather and suede boots and shoes. For women, a variety of styles, from heeled, knee-high boots to riding boots, are popular. (For that extra European touch, wear your boots over your pants, the better to show off that beautiful leather!). This season, short, stitched leather booties, paired with pants, are also very trendy at the moment.

Remember to be sure to pack a pair of waterproof or water-resistant shoes, too. You won’t want to have to run back to the hotel to change during snowy and rainy days!

Pile on the accessories, especially a beautiful bag and scarf

A carry-all bag is a must for travelers – and to blend in with the locals, try a large leather cross-body or shoulder bag for a daytime look. That advice goes for not only women, but men! Italian men aren’t afraid to carry a small bag or briefcase during the day to store items like cameras and books. (Fanny packs are rarely used in Italy, and even backpacks are usually used by students only).

Hats, scarves and gloves not only add a cozy and sophisticated touch to any look, but also help you keep warm with fabrics like wool and cashmere. A pair of well-fitting leather gloves lend elegance to any outfit. Don’t be afraid to  try all three together for a stylish, and functional, look on a cold day.

Finally, pile on the jewelry to spice up any outfit with both subtle and statement pieces, like gold or gemstones.