12 Italian Fashion Mistakes to Avoid Visiting Milan

One of the questions I get asked the most as an American living in Italy is, “What should I wear to fit in?” I get it. The idea of Italian style can be pretty intimidating, especially in Milan, one of the biggest fashion capitals in the world.

While I love hearing American-accented Italian on the streets, sometimes I can see my fellow countrymen coming from a mile away with their glaring fashion faux pas. That was the case recently, with tourists flocking to Milan for the Milano Cortina Olympics; I saw my fair share of fashion mistakes—so now I’m here with some helpful tips about what travel clothes to pack if you’re visiting Italy soon. Italian style favors dignity over utility, so zip away cargo shorts and practical trekking sneakers are enough to have many Italians spitting out their espressos. From patent leather loafers to wear-anywhere two-piece sets, these 12 Milan-approved fashion finds belong in your travel wardrobe—for a trip to Italy and beyond.

Best Milan Fashion Finds, According to a Local

Don’t wear: A full athleisure set as day wear

Wear this: A knit set

While pilates gyms are on the rise here, looking like you’re heading to or coming from pilates class is not. Instead of wearing a full-on gym outfit, try a luxe knit two-piece set that’s just as comfortable but a little bit more elegant. As a writer here, I live in cashmere loungewear that’s flexible enough for whatever the day brings: writing in my house, picking up my kid from school, or heading to aperitivo.

Don’t wear: A heavy-duty hat

Wear this: A chic fedora

I just came back from the cold freeze in New York—I understand the need for a trapper hat, but unless you’re in the mountains, Milan’s winters rarely get extremely cold. An elegant wool, wide-brimmed hat will keep you warm and stylish. There’s a bit of mountain glam influence with elegant women here pairing these hats with big faux fur coats or long camel hair overcoats.

Don’t wear: A too-athletic-looking sneaker

Wear this: A stylish walking shoe

Though there is the classic trope of the American or Northern European tourist in an unflattering sneaker, a stylish sneaker is often well incorporated into Italian style. Go for a retro-influenced option, like these Nike Pacifics that look great showcased with a cropped wide-leg jean or barrel-legged pants.

Don’t wear: Towering heels

Wear this: Patent leather loafers

From a driving shoe to the horsebit embellished, the fine leather Italian loafer is a major cultural style export. Worn with black tights and a skirt or jeans and a sweater, these Franco Sarto patent leather Carolyn loafers offer an elegant touch for safely navigating cobblestoned streets. With cushioning inside, reviewers find these shoes comfortable with plenty of arch support.

Wear this: A block heel boot

From the time I studied abroad in Milan, I’ve come to appreciate the versatility a beautiful leather boot adds to practically any outfit. These streamlined Imily Bela Ankle Boots are another good alternative to heels, because despite the 3.4-inch height, the block heel design won’t cause you to wipe out on the uneven cobblestone. Plus, the pointed toe adds flair, and the slip-on design makes them easy to put on and take off.

Don’t wear: Utility or cargo pants

Wear this: Relaxed trousers

Although my Patagonia fleece is now popular and trendy in Italy, these more practical types of clothes are often uncommon in Milan. Instead, there is an Italian preference for dignity over utility in wardrobes. I know those zip-away utility cargo pants are practical, but try these smarter pull-on trousers from Everlane in tailor twill. The drawstring waist and the wide leg add a sportier vibe, making for the comfiest polished pants in your wardrobe. Pair this relaxed fit Everlane tailored blazer with the pull-on trousers for a Milanese-inspired suiting look. Elegant and cool, this is the perfect city exploration outfit that will have you looking like a local.

Wear this: Well-tailored Denim

Italy has a long history with denim and jean-making, and a great pair of quality denim is another alternative to more utilitarian pant styles. The Levi’s resale market is extremely popular here, and these Levi’s Rib Cage jeans are the perfect weight and style, reminiscent of straight-leg vintage cuts. Wear this with a button-down for a put-together casual look.

Don’t wear: Oversized college hoodie

Wear this: A knit hoodie

No one cares that you went to Wharton, so you can put away that Penn sweatshirt. Though an artfully styled college sweatshirt in a Princess Diana style reference is cool, it’s not really appreciated here. Instead of that old college hoodie, try a more elevated knit one, like this Zella wool and cashmere rib hoodie that is just as casual and comfortable but more thoughtful than “I just threw this on.” Or, check out the budget-friendly $20 Amazon Essentials soft pullover. The point of style here is to make an effort—and look like it.

Don’t: Underestimate the power of accessories

Do: Take advantage of silk scarves

Don’t be afraid to channel la dolce vita with a beautifully printed silk scarf. Italians seemingly live in fear of colpo d’aria—a sudden cold blast on your neck that they say will cause your muscles to cramp up or you to get sick. Needless to say, scarves will never go out of style here. When I see a colorful, vibrant silk scarf, vintage or new, like this J. Crew Long Printed leopard print scarf, I snag it. Whether you’re on the streets of Milan or on a boat off the Amalfi Coast, always pack a silk scarf on your Italian travels.

Do: Make a statement with your sunglasses

Earlier today, I went outside without sunglasses because it was pretty much overcast. Big mistake—I felt naked! Statement sunglasses are a quintessential part of the Italian wardrobe, even on gray days. To make a statement without going overboard, try these off-white, exaggerated cat-eye sunglasses that are guaranteed to put your entire look together with their retro-inspired design.

Don’t wear: Obvious logos

Wear this: A classic shoulder bag

Logomania feels pretty passe here, with many Italians appreciating locally-sourced fine leather craftsmanship over mass-produced goods. I love the classic simplicity of this Quince Italian suede crescent shoulder bag (or the similar-looking, wallet-friendly suede bag from Amazon). This shape will never go out of style and is perfect for everyday use; the suede fabric can make an outfit.

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