I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (2024)

As a writer and digital entrepreneur living in Northern Italy, I’m inspired most days I step outside of my apartment. Being so close to one of the style capitals of the world in Milan has strongly influenced my style game, even as far back as college when I studied abroad there. These days, I take a cue from Italian fashion that embraces versatile classics, detail to fabric, genuine leather, and tailoring — and I dress to impress.

The secret? Since living here, I’ve embraced a “Why blend in?” state of mind. Like everything else in Italy, style varies greatly by region, you can’t expect to blend in with the glitterati with the same looks in Milan exploring the chic Brera district as say Capri, celebrity yacht-spotting. Whatever region I’m in, I know Italians appreciate great style. And wherever I am, I know I can’t go wrong with a great pair of sunglasses.

From a stylish silk scarf styled the Italian way for less than $20 to a classic, wear-anywhere black dress that practically begs to worn at a café while sipping an Aperol spritz, I’ve rounded up Italian looks that are in constant rotation in my armadio (that’s wardrobe in Italian). Practice! The next time you’re sipping a cappuccino, at a cafe in front of the Trevi, the waiter will wonder, what is this stylish Italian woman doing here? I’ll give her the Italian language menu!

Bold Sunglasses

A good pair of sunglasses is the building block of any basic Italian look, and only on a rainy day do I leave home without a pair. So important are sunglasses to Italian style that the first sunglasses with UV filters were produced in the 1600s in Murano, Italy and to this day, some of the biggest sunglasses manufacturers in the world are headquartered in Italy. While I have a lot of sunglasses in my rotation, my Italian-made, foldable classic Ray-Ban Wayfarer certainly gets the most love. Foldable, they’re great for travel and have joined me around the world. The polished black nylon frame fits most face shapes, but they also come in an XL — my husband has a bit of a moon face so that size is best for him. The Wayfarers are not too flashy but a subtle nod to style.

However, when walking the streets of Milan, shopping Via Spiga, lunch in Brera, I lean towards bold and flashy — fashionable and glamorous choices like these black Versace acetate stunners with the gold Versace medusa on the side. Of course, Versace is a classic Italian brand that’s been worn by celebrities including Elizabeth Hurley to rapper Biggie Smalls in the ’90s, and it’s consistently solidified itself as a go-to for bold taste makers.

To buy: sunglasshut.com, $173 (originally $345); amazon.com, $163

Superga White Sneakers

During those long days navigating Italian cities and towns, a comfortable sneaker is an absolute must (bonus if it’s stylish). Italian iconic footwear brand Superga has been around since 1913, evokes that effortless Mediterranean vibe and looks good on everyone. Even Kate Middleton has been spotted wearing them. A little bit more versatile than a Topsider, Superga is the ultimate summer sneaker. Retro inspired, it’s versatile enough for all seasons and looks right at home on the streets of Italy.

To buy: amazon.com, $69

A Beautiful Sciarpa (Scarf)

Yes, Italians (and myself) actually ride Vespas a lot when the weather is good in Italy. My husband and I rarely use the car in the summer unless we’re traveling long distances. As cliché and retro as it might have seemed in The White Lotus when character Tanya was glammed up and channeling Monica Vitti in big sunglasses and a scarf, it’s the dream scenario for a reason. Since moving to Italy, I’ve scoured vintage shops for classic Gucci scarves.

But the fabulous thing about this piece is you don’t have to go as far as Gucci. For less than $20, Amazon has a great selection of patterned scarves that achieve the same look for a fraction of the cost. Wear it the Italian way: A scarf around the neck elevates even a white T-shirt. Then there’s the glam Capri-inspired head scarf look. Or a quickly tied chic sarong at the beach bar! There are so many options. (Even though I live in Italy, I still have pinch-myself moments when wearing one that make me feel like a grande bellezza Italian film star.) Whether tied around your head — great protection from helmet hair — or around your neck blowing in the wind – be sure to do a double knot, and the sciarpa will complete your Vespa look.

To buy: amazon.com, $17 (originally $20)

Leather Jacket

Any other clothes you should consider for your Vespa look? Yes, a beautiful Italian leather jacket for those post-dinner rides. I actually never got use out of a motorcycle jacket until I moved to Italy. The double zip-up panel and high collar serve as a great defense against the wind. I finally saw the function of the fashion here! My Blk Dnm leather jacket, similar to this one from Saks Fifth Avenue, has traveled all over the world with me, and I find it the perfect Vespa jacket to throw over a dress or with jeans while on the go. My husband has a similar style, and when we’re going for a motorcycle ride we’ll often unwittingly wear the same thing.

To get the look for less, consider this Sam Edelman leather jacket from Nordstrom — I can’t believe the great deal since it’s 44 percent off. I’m even considering grabbing one in cognac. Customers rave about the buttery soft leather that’s perfect for layering and the quality at such a great price. I love the ample pockets for storage too!

To buy: nordstrom.com, $200 (originally $360)

Little Black Dress

The surest way to live la dolce vita? You can never go wrong with a black linen A-line dress in any situation, and this effortless style is a go-to from dinners out to apertivo in the sun. This classic, breezy option from Amazon is highly rated with more than 3,500 five-star ratings and is just bellissima.

To buy: amazon.com, $43 with on-site coupon (originally $58)

A Great Sun Hat

The Italian sun is intense, so a great hat will indeed do you well. What’s more, it’s all the rage —even Italian “peaco*cks'' (menswear aficionados often photographed at Pitti Uomo, Florence’s biannual fashion fair) are decked out with immaculate accessories, topped off with hats. From Como to Sicily to Sardegna, Crema or Umbria, you’d be hard pressed to find me exploring Italy in the summer without my now-sold-out Eric Javitz straw fedora — an Oprah fave. I even customized it for my life in Bergamo by adding straps that I tuck in while wearing. I ride on my husband’s Vespa a lot, and this was my easy solution to keeping it secure while on the go.

For a similar look, I’m eyeing this Madewell wide brimmed straw hat with a beautiful leather neck strap for this summer in Sardinia. This hat transitions perfectly from pool or seaside to exploring beautiful towns and the wide brim will give me the perfect temporary respite from the sun.

To buy: madewell.com, $58

The Perfect Pair of Jeans

Did you know that denim was invented in the Italian city of Genoa (Genova in English) in the early 16th century? Imported to the UK, it was marked ‘bales of clothe from Jeane’ a spelling adaption to the English pronunciation. From there, we have the origins of jeans as we know it, and denim through the way of France. And for your day-to-day in Italy, you’ll want a great pair of jeans. While Diesel and Guess jeans have become synonymous with Italian denim wear over the years, I prefer more classic styles.

I love 100 percent cotton straight-leg jeans that skew towards a wider leg, getting a pair from Zara in Bergamo a few years ago that I consistently get compliments on. Similar to the relaxed leg of these pair of Zara jeans, I often simply pair these jeans with the classic white T-shirt look and a scarf around my neck to elevate the look. Also, Gen Z —I disagree that skinny jeans are dead! If skinny jeans work for you, like this Levi’s 311 shaping pair, embrace them. They are perfect for a boot tuck in and a no-fuss look. A great pair of sneakers or a classic leather Italian loafer with a pair statement sunglasses? Che bella!

To buy: amazon.com, $44 (originally $70)

Carry-on Luggage for the Train

Taking high speed trains in Italy is a breeze, so I find myself on Italian trains a lot. Florence for lunch? See you there! Visiting my godmother in Rome? We’ll meet for a Vatican tour! And I’m back in Bergamo for dinnertime. Weekend trips and overnight trips, train travel in Italy really had me step up my carry-on luggage game, and in particular, my weekender bag. I spent years with a beloved Ferragamo perforated leather white carry-all that I snagged at a sample sale, but when looking for a luggage refresh, I wanted something just as elegant, but a little bit more susceptible to wear and tear.

Stella Jean-Inspired Dress

Sure, names like Ferragamo, Gucci, Armani are synonymous with Italian fashion. But, if you’re really in the know, you know Stella Jean the Roman designer that’s Giorgio Armani’s protegé. You’ve probably even seen the designer’s colorful statement pieces on celebs like Beyoncé, Zendaya, and Rihanna since these bold patterns and modern feminine aesthetic have caught the eye of the international fashion set for more than a decade. More often than not, these pieces are in collaboration with international craftsman through Stella’s Laboratorio delle Nazioni. Stella Jean has worked with women through the world, from the Kalash Valley in Pakistan to Burkina Faso to Peru promoting sustainable economic development in these communities.

Here’s a perfect Stella Jean dress for everything from a garden party to a summer wedding. It’s the perfect mix of a Roman businessperson style seen in the banker stripes and sciuraglam – think those glamorous women that seem to be in perpetual aperitivo mode – of a beautifully patterned silk skirt. Stella Jean’s looks always read elegant and stylish, and I’ve literally stopped traffic in both New York and Milan wearing one of her dresses. To get the look for much, much less, try this Amazon Vintage A-line flare dress with a bold pattern for just $35.

To buy: amazon.com, $35

Tailored Two-Piece Linen Set

Pairing menswear-inspired suiting with a classic sneaker during the day and a great heel with statement jewelry to transition to aperitivo is a favorite of mine, especially in warmer weather. It looks effortlessly pulled together. Plus, these timeless, comfortable linen separates are a perfect travel look, harkening back to the golden age of travel (think: The Orient Express). Belmond trains are now running an elegant train service from Venice to cities like Amsterdam, Paris, and Geneva —the perfect excuse to wear one.

For a menswear-inspired interpretation, look no further than powersuits that scream Armani, like Reformation’s Cienna linen vest, fitted like a top paired with the wide leg Vesta pant. Or choose a linen blazer; I love the double-breasted tailoring of this airy Palma linen option from Banana Republic. Better yet, for a relaxed vacation-ready interpretation, try a two-piece linen suit like this one from Abercrombie that give off an effortless yet put-together style.

To buy: abercrombie.com, $110

Gucci Loafer Lookalike

Whether it’s Ferragamo, Tod’s, or Valentino, few pieces are as synonymous with Italian style as a fine leather Italian loafer. And thanks to the recent House of Gucci film, the iconic butter soft Gucci Jordan loafers have had a strong resurgence, taking the fashion world by storm.

Although Gucci loafers can cost you up to $1,000, you can get the look for less at DSW. For less than $100, get the Vince Camuto Elpia Penny Loafer to complete your Milan-inspired look. In a very stylish patent-leather, the thicker sole of these Vince Camuto loafers are on trend with the lug sole style that are perfect for hitting city streets, trains and airports.

To buy: dsw.com, $80 (originally $110)

Statement Crossbody Bag

In Italy, the statement crossbody bag reigns supreme with generations-old luxury design houses still controlling the market on beautifully made local leather products. From Bottega Veneta to Prada, this is one luxe souvenir from Italy that will last years to come and get tax back at the airport. Admittedly, even before Italy, I was a designer bag enthusiast, with well-made crossbodies being my go-tos for day to day wear. I also usually stuff a reusable bag in there… you never know where you might stop!

A fun update for the summer is the Tory Burch Miller Pop Edge Mini Crossbody bag in Moroccan Blue. I’m rarely digging through my bag to get something with this bag. I love the high quality pebbled leather and the contrast stitching on the thick strap. Get the bold look for less at Amazon with this highly rated crossbody that tops off any outfit. I love a small discreet bag but am perpetually organizing so the double zip pockets allow room for my wallet, keys and phone in separate compartments.

To buy: amazon.com, $29 (originally $35)

Italian Skincare: Acqua e Sapone

There’s an Italian no-fuss skincare philosophy called acqua e sapone, literally meaning “soap and water.” It highlights the ideal of the fresh-faced look. The base of this is good skincare. No, Italian women do not slather olive oil all over themselves (although it’s a good base for natural skincare and hair care products) but Italian beauty companies like Davines reign supreme in the natural beauty industry. I discovered Davines, whose products are all made in Italy, while living in the UK and searching for natural hair care products without harsh chemicals. The Davines Nou Nou hair mask, with its Brindisi tomato base was my introduction to the brand, and I haven’t looked back.

Some of the most iconic pictures of an Italian holiday show bronzed skin and beach umbrellas. And it is a very sunny peninsula. A great way to combat hours in the Italian sun, or any sun actually, is Davines SU Aftersun hydrating gel. Fans love the smell of the product and its aloe-based relief after a long day at the beach, providing intense hydration to go with your holiday bronze.

To buy: us.davines.com, $36

Statement Jewelry

From leather necklaces from Dodo to a bold co*cktail ring a la Sofia Loren, statement jewelry is definitely an Italian style I embrace. Recently, while in Rome, someone regaled me with the story of seeing Sofia Loren and her amazing jewelry, namely her brilliant emerald, diamond, and ruby co*cktail ring of the Italian flag. But let’s start small.

One of my favorite places for statement jewelry is actually from J. Crew, and some of their bolder statement pieces like these jewel-toned teardrops are made in Italy. You can’t go wrong with a gold statement piece like these gold toned lightweight sculpted hoop earrings from J. Crew either. They look good with everything, from a slip dress in the summer to that Scaglione beige cashmere turtleneck to the classic T-shirt and jeans.

To buy: jcrew.com, $48

Italian Cashmere Cardigan

Italy produces some of the finest cashmere in the world. It’s a fact, but I am a bit partial. My husband’s family is a third generation knitwear company that creates both their own brand and knitwear for some of the top luxury houses in the world. For most of the year, my go-to Italian look consists of a beautiful cashmere piece – in the summer, maybe cashmere and silk.

There is nothing like a cashmere turtleneck. And with coastal grandmother chic and understated luxury a la Succession, I stacked up on expertly fitting cashmere turtlenecks, adding another color to my wardrobe every season. I pair them with mini skirts for a mod look, or great leather pants. In the spring summer season, taking me from Northern Italy summer evenings to New England nights – and the plane in between, I love this Scaglione Maxi Cardigan. A cashmere, cotton and linen blend, they are constantly restocking it as it’s the perfect throw on. The perfect transition piece, this will look just as tasteful over a white summer dress or linen pants as with a pair of wool white pants in the fall.

Prefer to wait for your Italian cashmere until you get to Italy? Totally understand! Here’s a budget-friendly polyblend from Amazon that gives you that great oversized cardigan look for just $28. It’s the perfect low commitment way to incorporate the style into your wardrobe.

To buy: amazon.com, $28

Knee-High Leather Boots

One of the earliest and strongest Italian style influences that I can remember is boots. A Chelsea boot, an ankle boot, a knee high boot. Italians seemed to love boots and even before Stuart Weitzman thigh grazers took the fashion world by storm, Italians had a love affair with a beautiful leather boot.

One of my go-to boots that always gets a “tesoro che chic!” is a vintage knee high black with gold hardware Saint Laurent pair that I have, similar to this Gucci pair. But amore! You can definitely find this look for less without compromising on the quality with this black leather pair from Zappos.

Running through many Italian cities, you’ll find that some of the most charming areas are cobblestoned. These cobblestone streets keep my cobblers in both the US and Italy in business. Better than my stiletto heeled knee high boots, the block heels are comfortable and perfect for tackling metros, trams, and the cobblestone streets of Italy in between. The style hits right below the knee and is perfect for pairing over a pair of jeans or with an elegant skirt.

To buy: zappos.com, $250

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