15 Italian Winter Fashion Styles for Travel

As a New Yorker, I’ve attended New York Fashion Week since my teenage years. Once I became aware of European fashion shows in London, Paris, and Milan, I eagerly followed those as well from afar. The fall and winter collections coming out of these cities were always my favorite, whether it was the luxurious abundance of Italian leather or seeing ethereal chiffon collections mixed with winter knits float down French runways. 

I always kept an eye on what Europe was doing, and, now that I live in Italy, I see firsthand how the runway looks translates into the streets of these fashion capitals. They’ve influenced my style as well: the boot, chiffon skirt, and turtleneck pairing I “learned” in Paris, or the appreciation for a wool trouser gleaned from the Brera district in Milan. 

From an amazingly-priced bomber jacket to a pumpkin-spice-inspired plaid fringed skirt, I’ve gathered a few winter fashion styles that I’m already seeing sported in European cities. 

Best Overall Fashion Finds

Quince Italian Wool Straight Leg Pants

Quince

Living in Europe has given me a strong appreciation for a beautifully tailored trouser. These pants feel like a power move and are crafted from soft Italian wool with a sleek, straight-leg cut that gives you polish without feeling stiff. The elasticated back waist means they look tailored, making them a dreamy work-to-weekend staple. They’re great for traveling and look cool when paired with a pair of sneakers and a fitted cashmere sweater. 

Tanming Women’s Plaid Fringe Midi Skirt

Amazon

Mixing tartans and plaids is a hallmark of the beautiful fall style, especially in Europe. I’m currently debating a plaid style similar to this fringe midi at Amazon. Paired with a knee-high suede boot and a sweater, this is a perfect look for a fall day.

Ann Bully Hobo Bag

Amazon

I love a gorgeous leather handbag and add to my collection very carefully. I still have vintage Coach bags from my mom’s collection in the ‘90s. A compact shoulder bag is my forever go-to: it’s sleek, hands-free, and holds only what you actually need. Lately, instead of splurging on the latest “it” shapes, I’ve been reaching for more affordable, under-the-radar options that still look elevated. This hobo bag has that same clean, structured silhouette you’d see on the streets of Milan, but at a much friendlier price point.

Travel + Leisure

Express Oversized Faux-leather Bomber

Express

There’s nothing like Italian leather, but it is expensive, so if you want to look luxe for less, reach for a faux leather jacket. A style that I’m seeing a lot on the streets lately is a ‘90s throwback to the leather oversized bomber jacket. This loose option is great for casual layering or adding a touch of edge to a more feminine look. The under-$100 price of this Express Faux Leather Bomber makes it even easier to try the trend without having buyer’s remorse. 

Madden Girl Shakke Boot

Zappos

A beautiful knee-high suede boot is a winter must, and in the last few years, many winter styles have been influenced by western embellishments for an Americana touch. I love the fringe on these Madden Girl knee-high boots. The low heels are a wearable height for the day that easily transitions into the evening. Pair them with a midi skirt (with a little bit of flare at the hem to accommodate boots) and a chunky sweater for an elegant and timeless look. 

Quince Cotton Cashmere Ribbed Turtleneck

Quince

While living in London years ago, I fell in love with the modern style of a black mockneck and patterned mini skirt. It’s still a classic look. This Quince cotton mockneck has just a touch of cashmere for ultra softness, and the bodysuit style makes for a smooth, clean tuck into bottoms or when layering. Pair it with everything, from a chiffon skirt to jeans, or under a sweater vest. 

Viligo Faux Leather Trousers

Amazon

Leather culottes are having a moment in Europe. These straight-leg faux leather pants from Amazon give cool vibes without the designer price tag. They’re styled to look polished but feel comfortable enough for day-to-night wear. Pair them with a crisp white tee and blazer for brunch or swap into low pumps for drinks. 

Levi’s Women’s High-rise Skirt

Macy’s

You don’t have to put away that perfect summer denim skirt yet. Instead, dress it up with a great boot and a chunky knit for an early winter look. This Levi’s women’s high-rise, back-slit skirt gives that great denim quality that you’ll feel great in for years to come. Honestly, I’ve taken it a bit to the extreme, pairing my denim skirt with cashmere socks and (designer!) hiking boots for a trip to a glacial lake in the Italian Dolomites. 

Caslon Miller Lug Chelsea Boots

Nordstrom Rack

Stylish winter boots are a must here. Often, you’ll want a waterproof, lug-soled Chelsea boot in a posh leather style that looks just as elegant as it is durable. These Caslon Miller Lug Boots from Nordstrom Rack do the trick and cost way less than designer options.  

Steve Madden Button-up Dress

Nordstrom Rack

The little black dress is intrinsically linked to Parisian chic. Recently, I packed my La Ligne Ivo Dress for a day of meetings in the French capital, and I can’t tell you how many compliments I received on it. You can snag a similar option for less, like this one by Steve Madden. Paired with a ruffled silk blouse underneath, tights, and loafers, I felt the epitome of Parisian chic. 

Banana Republic Factory Timeless Topcoat

Banana Republic Factory

Heading to a formal event or running errands in jeans and a baseball cap, and a beautifully tailored overcoat makes all the difference. The attention to detail on this Timeless Topcoat coat gives it the appearance of truly luxurious tailoring. 

Travel + Leisure

Old Navy High-waisted Barrel Corduroy Pants

Old Navy

There’s been a huge style resurgence of preppy staples like corduroys in rich earth tones. I love seeing Milanese women borrowing American style influences and pairing camel corduroys like these Old Navy barrel pants with lug-sole moccasins and a great blazer.  

Nia Vetiver Embroidered Maxi Dress

Nordstrom

I’ve always loved the rugged, romantic pairing of a floral chiffon dress with a boot. This embroidered maxi dress is a great wintery floral to try, and it comes in versatile colors that look great all year-round. Try it layered with an oversized chunky knit sweater and a pair of boots, or, like I saw in Paris recently, paired with a corduroy blazer for aperitifs.

iScaglione Shine Alpaca Turtleneck

Scaglione

While I was in Paris, a few knitwear moments caught my eye. Both in a bistro and in a bar, two people were wearing dark sweaters, but they dazzled and caught the flickering candlelight of the room. One had subtle sequins the same color as the knit, and the other was sewn with a kind of high-shine thread. I love incorporating a sparkle beyond the holiday season, and this Scaglione Alpaca turtleneck does just that. The shine effect against the navy gives the impression of night stars. It’s a fun way to wear that winter staple of a cozy turtleneck.

Travel + Leisure

Ray-Ban 58mm Wayfarer Sunglasses

Neiman Marcus

I live in Italy. It’s always sunglasses season, but during the winter, I do tend to gravitate towards darker and more classic colors or shapes. Arguably, the best sunglasses purchase I’ve ever made is the Ray-Ban Wayfarer, a truly timeless shape that never goes out of style and looks great.

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