5 Italian Fashion-inspired Winter Travel Outfits

Packing for travel is always a little harder because there’s less suitcase space to work with, so you definitely want to make sure those bulkier items are really working overtime in your luggage and will be useful during your trip. With beautiful sites like Saint Peter’s Square covered with a sprinkling of snow, Venice’s canals lined with fewer crowds, or the picturesque, ski-ready Dolomites, Italy can be an amazing winter destination—and this American living in the Bel Paese is here to tell you exactly how to dress for it. 

World-renowned for its cashmere, buttery leather, and tailored wool, Italian winter fashion leaves no room for dowdy sweatpants and sweatshirts. From luxurious staples that you’ll wear every day to showstopping but still winter-friendly Milanese maximalist dresses and coats, these five mix-and-match travel outfits channel that effortless Italian style for your cold-weather trips and are worth every inch of space in your suitcase.  

Outfit 1

Quince Mongolian Cashmere Turtleneck Sweater

Lululemon Daydrift High-Rise Wide-Leg Trouser

Quince 100% Merino Wool Shawl Collar Long Coat

One of Italy’s most famed exports is fine cashmere with fashion companies from around the world heading to Italy to produce their knitwear. Every season, I stock up on closet cashmere staples that add a refined and elegant touch to my outfits. Right now, I love a neutral cashmere that’s slightly loose like this Mock Neck Raglan Supersoft Sweater from Scaglione (Quince’s Mongolian Cashmere Turtleneck Sweater is a budget-friendly alternative), which creates a timeless wintry outfit when paired with something chic like these wide-leg trousers from Lululemon. Super-comfortable with the brand’s stretchy Luxtreme fabric, these pants are comfortable enough to fly in and elegant enough to head from the meeting to an airplane. 

Top this look with an oversized overcoat like this style from Quince (or this discounted one from Amazon). With a shawl collar and merino wool fabric, this coat is not only extremely warm and cozy but also the ultimate sophisticated topper. The stylishness and comfort of this look are behind its effortless beauty; great fits and classic pieces are the hallmarks of Italian style. 

Outfit 2

Simplee V-neck Velvet Maxi Dress

There’s a certain Milanese style set that leans maximalist and embraces the bold colors and patterns of Italian life. The brand La DoubleJ is known for its extravagant pieces, ranging from homeware to clothing, showcasing the glamour found behind the gilded doors of Milan’s most elegant homes.

I have my eye on this Camerino-inspired printed La DoubleJ smocked maxi dress, which is a statement piece that also is easy to pack, but you can easily achieve the same sultry, velvety look with this $41 lookalike at Amazon. You’ll be sure to stand out during a beautifully lit aperitivo. Pair either dress with beautiful knee-high boots like these Naturalizer stunners (more on them below) for a cool boho outfit.

Outfit 3

Everlane The Boxy Sweater in Everyday Cotton

Daze Far Out Faux Leather Wide Leg Pants

Part of the effortlessness of Italian style is the quality of the raw materials—I mean taking basic shapes and style ideas but using luxe fabrics. Italians have a strong appreciation for the chicness of French-inspired stripes (it’s one of the few wins they’ll give the French). Try styling this La Ligne sweater or this lovely Everlane sweater for the perfect loose fit that isn’t too long. 

Looser-fitting leather pants are the ultra-modern style I’ve seen on the streets of Milan recently that I’ll be wearing this winter. I do have a few pairs of skinny black leather pants, jeans, and leggings, so to try this new fit, I decided to go with these wide-leg leather pants. The preppy style staple is an unexpected pairing with something as edgy as black leather pants, but the flat front, side slit pockets, and clean wide waistband add smart tailoring to these relaxed travel-friendly bottoms.

Outfit 4

M.M. LaFleur Leslie T-shirt

Quince Brushed Cashmere Shrunken V-Neck Sweater

Gap High Rise Wide-Leg Velvet Pants

Rich jewel tones are not just for the holiday season, and these velvet pants from Gap Factory are a more tailored alternative to your typical velvet loungers. The soft ivory color of this Quince shrunken v-neck sweater is a versatile choice, perfect for layering or letting the texture shine on its own. The fuzzy brushed cashmere effect of the sweater completes the luxe, touchable fabrics of your look.

Pair your sweater with a high-quality T-shirt underneath for that cool, effortless touch that also works double duty in your suitcase. Sometimes, as the temperatures outside go down, heaters are at a high, and if you have to take off your sweater, you’re going to want something that stands on its own. I’ve had this M.M. LaFleur cotton T-shirt for years and I get countless compliments on the fit and the durability. Made with Peruvian Pima cotton in a tailored shape, this T-shirt has maintained its collar shape and overall form throughout the years.

Outfit 5

Intimissimi Modal Cashmere Ultralight High-neck Top

Levi’s Ultimate Western Button-up Shirt

Gap High Rise Wide-Leg Sweatpant Jeans

Abercrombie Reversible Vegan Suede Shearling Long Coat

Italian style incorporates a bit of neo-Western influence too. Big shearling-lined utilitarian jackets and fringe details are huge right now. Few brands can do a denim shirt better than Levi’s, and its Ultimate Western Shirt is the perfect layering piece for your wardrobe this winter. The rugged Americana style is much appreciated here in Italy and with Yellowstone streaming in Italian, the Dolomites as well be our Big Sky. 

When you need to get your outfit out and about-ready, you can make it a little more rugged with distressed bottoms like the Mother The Dodger Sneak Jeans in durable hard denim or the Gap High Rise Wide-Leg Sweatpant Jeans. Then, break up the denim on denim with this thin modal Intimissimi turtleneck underneath the button-down. A perfect layering piece, it’s a suitcase M.V.P. for slipping under a blazer, a dress, or a sweater. 

To complete the look, you need some shearling, and a great brand to shop is another timeless purveyor of Americana style that’s experiencing major popularity here in Italy: Ralph Lauren. I have my eye on this sold-out Lauren brand faux shearling and faux suede coat that exudes elegance, but you can also channel it with the Abercrombie Reversible Vegan Suede Shearling Long Coat.

Best Winter Accessories for Italian Fashion-inspired Travel Outfits: 

Andre Assous Olivia Clogs

This year, clogs are back on trend with shearling-lined styles like this one from Andre Assous popping up in the windows of Italian boutiques this season. I love the slip-on comfort of the Olivia Clogs and think the ease of getting them on and off makes them the perfect travel shoes. Plus, the 2-inch block heels give you height while still being sturdy, and the cozy shearling interiors make them a warm option for the winter months with a great pair of cashmere socks and any of the aforementioned travel outfits.

If heeled travel shoes aren’t in the cards for your next trip, I found some equally stunning flat-sole options. Birkenstock’s Buckley Shearling Suede Clogs are the ultimate casual walking shoes, or you can opt for something easier to dress up like these waterproof Blondo booties. 

Naturalizer Kalina Narrow Shaft Boots

From my early student days in Italy, one of my earliest style takeaways was the importance of a great boot. Over jeans, with dresses and skirts, and so on, a beautiful knee-high boot always seems to be the finishing touch of every Italian woman’s outfit (they are sophisticated enough to elevate a look and add a subtle layer of warmth). I love the simple elegance of these Vince Camuto Avriah Boots with their 2-inch heels and padded soles, which make them just comfortable enough to wear for hours.

However, Italy’s cobblestone isn’t the easiest to walk on, especially when freshly lined with winter frost. Though I really appreciate the rubber tread on these Vince Camuto boots, I’d be remiss not to highlight a low-profile knee-high boot style like the ultra-supportive (and on-sale) Naturalizer Kalina Narrow Shaft Boots.

Gap Vegan Suede Slouchy Tote Bag 

Let’s face it, you carry around more in the winter and, though I’m a small cross-body girl, I really couldn’t do the micro mini bag trend. I’m happy the slouchy shoulder bag is having a major fashion resurgence as it’s the perfect option for daytime exploring. Tissues? You have those. Cough drops? Check. Sunglasses? Yes. An absurdly large phone? Check. Gloves? A beanie? Check. Check. This Gap Vegan Suede Slouchy Tote bag is a top contender for my winter travel purse as it can even fit a heavy laptop and still feel comfortable. The beautiful color and fabric mimic suede and, though it doesn’t zip close, it does sit close to the arm making it great for traveling. 

Sarto by Franco Sarto Riley Bit Loafer

A great loafer is another Italian style essential and the au-courant lug sole loafer silhouette is an ideal cold-weather option. As seen in this Sarto by Franco Sarto pair. The rounded toe makes these loafers a little easier to wear without the hassle of breaking them in. Pair them with any of the jeans or trousers above for a cool, wintry look.

Bombas Merino Cashmere Blend Rib Calf Socks

As someone who’s always cold, I love wearing cozy cashmere and wool socks all winter long. But, let me let you in on a little secret: Cashmere socks aren’t very durable and aren’t meant to be worn with shoes. So for that warmth and softness, I’d recommend a cashmere wool blend if you plan to wear these socks out and about. I’m currently loving these Arket cashmere-wool blend socks for durability and style, but you can get more color options with this cozy pair from Bombas. 

Quince Featherweight Cashmere Silk Frayed Edge Scarf

Whether you’re throwing it over your shoulder or around your head, a great silk scarf is my year-round Italian style essential. One of my favorite silk scarves is one I bought in Venice as a student almost twenty years ago. I’ve been eyeing this cashmere silk scarf from Lafayette 148, which is from the brand’s Save Venice capsule collection and is a beautiful way to break up tailored winter overcoats. A portion of the capsule’s sales will be donated to Save Venice’s “Women Artists of Venice” program. Similarly, Quince’s Featherweight Wool Cashmere Frayed Edge Scarf, $62, is stunning in many solid colors.

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