15 Best Winter Sale Italian Style Amazon Deals

Dressing like an Italian, whether for the spring, summer, fall, or winter really comes down to owning a couple of solid basics and some well-picked standout pieces to elevate your look. Think: velvet ballet flats, cropped leather jackets, and cashmere turtlenecks. As a travel writer from Rome, I’ve learned how to curate my wardrobe to be comfortable yet stylish and to stock it with versatile options that can be worn in multiple seasons.

Here, I’ve crafted an easy-to-follow list of some of my favorite winter Italian fashion staples, which are on sale during Amazon’s end-of-the-year sale, so you can dress as the Romans do. From leather touchscreen gloves to knee-high leather boots and belted wool trench coats, these are the 15 effortless Italian styles to add to your travel wardrobe this winter.

Levi’s Women’s Belted Faux Leather Moto Jacket 

A classic leather jacket is a must for any wardrobe, and if you invest in the right one, it can last you for years. Good leather jackets aren’t known for being affordable, so if you’re not quite ready to splurge you can try this budget-friendly Levi’s faux leather version currently on sale for $79. It features a cropped motorcycle fit and is available in a dizzying 46 colors, with sizes ranging from extra small to 3XL.

Cole Haan Women’s Flared Trench Slick Wool Coat

A stylish, belted trench coat, like this option from Cole Haan, is an ideal choice for staying prepared even in the most unpredictable of weather. It’s a classic Italian look that can be worn in the spring or fall, so it’s an especially versatile wardrobe item. This on-sale $56 wool version won’t break the bank but still offers quality that will last year to year. Pair it with either a cashmere turtle neck or a pair of flared pants for an effortlessly chic look, my go-to since it helps elongate my petite frame.

Naturalizer Women’s Kelly Velvet Mary Jane Flats

Velvet ballet flats, known in Italy as friulane, are a universally worn shoe in the country. Originating from 19th-century Venice, they’re often worn by Italian women during every season and are very lightweight and comfortable (more so than sneakers, in my opinion). I have six pairs in bold colors including fuschia, yellow, orange, and two shades of green, and I love the bright pop of color they give to my casual or formal outfits.

I often purchase my pairs in small boutiques across Italy or from the popular Italian brand ViBiVenezia, which ships to the United States. If you’re looking for a more affordable option, consider this Mary Jane option on sale for $100.

Happy Sailed Womens Tweed Blazer

An oversized blazer is a key piece to any Italian woman’s wardrobe and can be paired with everything from heeled booties and sneakers to jeans and dresses. The boxier, relaxed fit is not only comfortable but also great for layering so you can wear it beyond the fall and into the winter and spring. I love this tweed option that’s a modern twist on a classic pattern, available in multiple colors including pink, beige, and black.

Franco Sarto Women’s Giselle Tall Boots

Crafted entirely out of leather, these knee-high boots from Italian fashion house Franco Sarto are the ideal boots to stay warm and look good in the winter. Also great to wear in the fall and spring, these boots would look especially good paired with a maxi dress or a short skirt and a long trench coat for an effortlessly sleek look. 

Pro tip: don’t forget to prime your leather with a boot wax to protect your shoes from the elements, especially if you find yourself in an area prone to flurries or rain. 

Anrabess Two-piece Sweater Set

Athleisure is still a relatively new concept in Italy, so when Italian women wear a matching sweatsuit set, it not only needs to be comfortable but effortlessly stylish as well. I mostly purchase my matching sets from Spanish clothing brand Oysho, but this traveler-loved Anrabess set from Amazon is a very close match to some of the ones I own and is a steal at just $41.

GreenMount Cashmere Sweater

If there’s one material that Italians love to wear in the winter it’s cashmere. It’s comfortable, elegant, and incredibly toasty while still being lightweight. While the luxurious fabric is not generally known for its affordable price tag, right now, it’s available in this simple but stylish cashmere ribbed sweater that’s on sale for $132. With various shades to pick from, it’s the perfect staple to dress up or down for whatever mood or occasion. 

Dsane Winter Leather Touchscreen Gloves

Wherever you go in Italy, you’ll often see Italian women of all ages sporting a pair of smart leather gloves. Not only do they keep your hands warm, but they have the added benefit of looking incredibly elegant. Crafted from sheepskin leather, this pair from Amazon is lined with soft, warm cashmere so that your hands can stay toasty and comfy. Shop them in beige or brown, red, and more color options. Best of all: they’re touchscreen-compatible.

Utenwat Crossbody Camera Purse

This minimalist but stylish leather crossbody purse is small enough to sit comfortably on your person while boasting plenty of organizational features for all your essentials. Inside, you’ll find a spacious main compartment with a zippered pocket large enough to fit a passport and four card slots. There are also two additional external pockets in the front and back. The bag is available in multiple neutral colors and features a removable and adjustable patterned crossbody strap. 

Pro tip: many stores in Rome sell removable and adjustable crossbody straps in various colors and patterns for less than 10 euros that you can purchase to mix and match your purse with your outfit.

Sojos Cat-eye Sunglasses 

Sunglasses are a must for winter days in Rome. While the city isn’t immune to gloomy, gray days, winter in Rome is usually very sunny. It’s not uncommon to see Italians strolling around with shades or donning them when having an espresso al fresco.  Cat-eye sunglasses are popular for their timeless elegance, and while mine were handed down to me by my mother, you can snag your own pair with this affordable style at Amazon that’s on sale for $15. 

Fengbay Corduroy Skirt 

Corduroy is in these days, and don’t let anyone tell you otherwise. This soft corduroy skirt is a fun way to dress up an outfit white still staying comfortable and warm. In the fall, winter, and spring, I love to pair skirts and dresses with a fun pair of patterned tights and knee-high leather boots for an effortlessly chic look. This affordable option on Amazon is available in five neutral colors, including black and coffee brown, and sizes ranging from S to XL.

State Cashmere Scarf

Scarves are a must-have in the winter, and this high-quality cashmere option is the perfect soft and warm accessory for the colder weather. Featuring a classic, minimalist design that’s timelessly elegant, it’s gentle on the skin and available in several neutral colors including navy and charcoal. 

Jaxmonoy Knit Beanie

For just $13, this slouchy beanie is made from a wool blend and is a stylish option for keeping your head and ears warm on colder days and nights. The material isn’t scratchy, so it won’t irritate your skin or cause unnecessary hair frizz. Plus, it’s compact enough to roll up into your purse or winter jacket coat for when you need it.

Free People Women’s Easy Street Tunic

This cozy ribbed cotton sweater from Free People is as cozy as it is fashionable. Featuring a dropped shoulder and split hem, the slightly oversized sweater can be dressed up or down depending on your mood. It especially looks great with jeans and is comfortable enough to throw on with a pair of leggings when traveling long distances.

Lands’ End High-rise Corduroy Pants

Corduroy pants are a comfy but trendy alternative to jeans or slacks for the fall. While I’m partial to this pair from Madewell (available in four neutral colors, including forest green, Bordeaux wine-inspired red, white, and chocolate brown), this budget-friendly option from Amazon is a close match. They’re a great transitional piece that can be worn in the fall, winter, and spring.

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