You’ll be out on the town a lot, so you’ll need something to protect you from the wintry cold. Enter the trench coat – an old favorite that keeps your whole body warm. Think dark colors. Steer clear of white; you don’t want to look dirty. Black is always in, and as a tourist, it’s best to blend in instead of standing out in bright colors, if only so you attract less attention from pickpockets.
A well-fitted blazer has a trendy look, and you can vary the top you wear under it. You can wear a blazer over trousers, a skirt or even a dress. This makes it perfect for mixing and matching on your Italian sojourn. Pair your blazer with a basic black long-sleeved shirt or a cute princess-cut top to add a little femininity.
New-looking black slacks are always hip in Italy. If it's really cold out, wear black leggings underneath. No one will ever know they're there, as long as the waist of the slacks is higher than the leggings, so you can walk around to your heart's content without freezing. The leggings won't make you too warm when you step into a cozy cafe for an espresso, like thermal undies can.
Lots of Italians wear jeans, but usually not old, baggy, torn ones. Opt for fitted jeans in a darker color so they don’t show dirt easily. Darker colors have a sleeker, more stylish look, too, especially in the winter when darker clothing is in. Wear a plain belt so you don’t look sloppy.
Dress and Skirts
You'll see Italian women in tidy but loose skirts that come down to the knees or lower. These are staples in any Italian woman's wardrobe. Wear leggings with them in the winter to keep warm. Just steer clear of mini-skirts. Fair or not, you might be disrespected by local dudes if you show up in a short skirt, and you'll be cold. Bring an elegant long dress in a soft fabric that gently clings to your body for evenings out; it's best not to show cleavage and to carry a shawl if the dress shows your shoulders.
Choose several scarves to dress up your winter look. Scarves are a hallmark of Italian style, always classy and practical in winter. Skip those fuzzy numbers that pop up at home in wintertime, opting for a soft knit or a velvet number for a little more flair. A scarf with a subtle pattern and maybe a little sparkle works -- think shiny thread used in the stitching or tiny rhinestones as accents in the pattern, nothing too noisy. Plain is always fine too, and so is silk, though it won't keep out chilly winds as well.
Well-broken-in boots will make you look chic in Italy and keep you warm in winter. For long days hitting up the sights, grab a pair of loafers that are really walking shoes in disguise. Lots of shoe designers are merging comfort with fashion now, so you’ll find sleek, dark numbers made of leather or faux leather. There’s no excuse now for bringing that old, worn-out pair of sneakers!