I’m an American in Italy, and These Are the 5 Effortless, Mix-and-match Travel Outfits You Need for Winter

Packing for winter 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 (psst: some are even on sale ahead of Black Friday).  

Outfit 1

Abercrombie Slim Turtleneck Sweater

M.M. LaFleur Kick Flare Foster Pants

Banana Republic Italian Melton Trench 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 cream or white cashmere that’s slightly loose like this Mock Neck Raglan Supersoft Sweater from Scaglione (Abercrombie’s on-sale Slim Turtleneck Sweater is a budget-friendly alternative), which creates a timeless wintery outfit when paired with something chic like these slim-line pants from M.M. LaFleur. Super-comfortable with the brand’s PowerStretch 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 trench from Banana Republic (or this double-discounted one from Amazon). Tied at the waist and with an offset button closer that finishes with an exaggerated collar, 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 trends maximalist and embraces the bold colors and patterns in Italian life. The brand La DoubleJ is known for its extravagant pieces ranging from homeware to clothing, showcasing the glamour that might be behind the gilded doors of the most elegant Milanese 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 $60 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

Jenni Kayne Chloe Crewneck Sweater

Madewell Low Slung Baggy 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 Oversized Cropped Marin Sweater or this lovely Jenni Kayne Chloe Sweater, which is a rare 25 percent off ahead of Black Friday, 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 Madewell Low Slung Baggy 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

J. Crew Brushed Cashmere Cropped V-neck Sweater

Madewell Superwide-leg Trousers

Rich jewel tones are not just for the holiday season, and these velvet trousers from Madewell are a more tailored alternative to your typical velvet loungers for the holidays. In a deep blue indigo, they can be your comfier winter jeans alternative. The bright poppy red color of this J. Crew Brushed Cashmere Cropped V-neck sweater is a must as pops of red knits seem poised to dominate street style again this winter. Not a fan of the hue? Then try the navy blue color that customers said has a beautiful glow for a stunning navy tonal look that can be dressed up. The navy on navy is a fun winter nod to the sartorial Milanese navy pinstripe suit. 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

Rag & Bone Miramar Sofie Sweatpant Jeans

Avec Les Filles Faux-shearling 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, which is majorly discounted during Amazon’s early Black Friday sale, 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 these Mother The Dodger Sneak Jeans in durable hard denim or the Rag & Bone Sweatpants 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 Lauren brand faux shearling and faux suede coat that exudes elegance, but you can also channel it with this Avec Les Filles Faux-shearling Coat, which is nearly $200 cheaper at Anthropologie. 

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 La Canadienne Always Booties. 

Naturalizer Brent Weatherproof Knee-high 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 Brent Weatherproof Knee-high 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 mimics suede and, though it doesn’t zip close, it does sit close to the arm making it great for traveling. 

Everlane The Lug Loafers in Black Croc Embossed 

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 Everlane pair, the chunky rubber lug sole has exceptional grip for winter city exploration and I love the little lift I get wearing these with my baggier jeans and trousers. The rounded toe at the front 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, wintery 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 Wool Cashmere 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 Lafayette148, 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, $70, adds stunning contrast with its subtle tiger-striped design (or, you can opt for a solid-hued silky option like this one). 

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