How To Dress Like An Italian Woman: Fall Edition

This season is filled with fun layering pieces, luxurious fabrics and sleek silhouettes.

Although we love island hopping in Sicily and sunbathing along the Amalfi Coast, autumn might be our favorite time to visit Italy. By October, the crowds have thinned (though only slightly!) and the temperatures drop in cities from north to south. The fall season brings truffle hunting, olive picking and some of the most spectacular rainbow-hued sunsets. And Italian fall fashion is filled with fun layering pieces, luxurious fabrics and sleek silhouettes.

From boyfriend blazers and vintage denim to all things leather, Italian women know how to make the most of the season creating street-style looks that are timeless and versatile. Here are our must-haves for the fall season. Looking for other seasons? Check out our summer fashion edition and 7 staples every Italian woman has in her closet.

The Leather Jacket

A leather jacket is a staple in any Italian woman’s closet and perfect for fall days and nights. Whether it’s a cropped jacket with minimal detailing, or a biker jacket with zips and hardware, this is an item you can easily dress up or down. We also love a spin on a classic, like this leather parka with a drawcord hem for a flexible fit, and hood for unexpected rainy days.

The On-The-Go Sneaker

Italy’s streets were made for walking, so you’ll want to wear comfortable (but chic) sneakers for sightseeing. Superga, an Italian shoe branded founded back in 1911, makes some of the coolest Italian sneakers with a touch of vintage and a lot of personality. Branded as “the people’s shoe of Italy”, every Italian has multiple pairs in a range of colors and fabrics. We love the 2750 Cotu Classic in white or black, though it comes in 23 shades to match any outfit.

Our tour guide friends in Rome also swear by FitFlops. These are the softest shoes you’ll ever wear which feel like walking on clouds. As soon as you slip your feet into a pair of Rally Sneakers, you’ll never look back (check them out in suede and leather).

The Boyfriend Blazer

A boyfriend blazer pulls together any outfit: throw it over a pair of jeans with a white t-shirt and you can go from a morning coffee date to a midnight glass of wine in the piazza. There’s just something about accented shoulders that really elevates your look. An oversized blazer is perfect for layering over shirts and sweaters on chillier days. This 100% organic cotton blazer by GANNI is a beautiful bordeaux color for the season. For something warmer, opt for a wool blazer in a neutral shade.

Tights Under Everything

Italians are known for lingerie, from chic La Perla nightgowns to silky pajamas from Intimissimi. So it’s no surprise that tights are a staple accessory in every closet – and an essential to round-out your Italian fall fashion outfits. Wear them under woven skirts and party dresses, or pair them with leather shorts or culottes for a statement. Founded in 1987 in Verona, Calzedonia has hundreds of tights to choose from, whether you opt for sheer, opaque or patterned tights. We love these cozy cashmere tights for day and switching into sheer glitter dot tights at night.

The Sleek Ankle Boot

While over-the-knee boots can be really sexy, there’s nothing easier than throwing on a pair of sleek ankle boots to match any outfit. Whether you’re wearing skirts and dresses, cropped denim or extra-long pants, a pair of black leather ankle boots will elevate any look. This pair by Geox, a brand known for its comfort, feature a timeless design that will last through the years. To make a bigger statement, these high block heel ankle boots by Aeyde are sleek and futuristic.

The Vintage Inspired Denim

Extra-long denim is everywhere in Italy these days. This sleek silhouette is a fun way to subtly show off a statement shoe like sparkly heels and brightly-colored boots. Based in Milan, The Attico is a brand with its finger on the pulse of the latest trends, like these cool long boyfriend jeans. If you’re looking for something roomier, check out these wide leg jeans by Isabel Marant.

The Shoulder Bag

Leather handbags are synonymous with Italian fall fashion, and they’re an accessory that only gets better with time. In the fall, you’ll want a spacious handbag to pack a pocket-sized umbrella and a scarf along with your essentials, so a shoulder bag is perfect. Crafted in Tuscany, this buttery-soft bucket bag by Cristian Marcucci has a roomy interior with adjustable shoulder straps and a luxurious suede lining. We also love subtle touches to classics, like this elegant laser-engraved handbag designed in Florence which has texture, clean lines and timeless style.

Don’t Forget Your Skin

The cooler temperatures mean your skin may need some extra pampering, so be sure to check out our 9 favorite Italian skincare and beauty brands. In Italy, la bella figura extends to skincare, beauty and hair routines. These quality products are clean, versatile, and 100% Made In Italy with nourishing ingredients.

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