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!

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (1)

Bold Sunglasses

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (2)

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (3)

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)

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (4)

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

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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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (6)

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (7)

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.

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (8)

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (9)

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (10)

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.

Everyone I know swears by the Béis Weekender bag, and after using it as my carry-on on a recent Europe trip, I completely understand why. With its sleek design, the Béis weekender is the perfect bag for the overnight or day trip. For the long days but short day trips, a stylish tote with room for whatever you may just pick up on your travels is a good option. The interior pockets also offer a good amount of protection from pickpockets – a must when venturing into more crowded touristy areas.

To buy: nordstrom.com and beis.com, $108

Stella Jean-Inspired Dress

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (11)

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (12)

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.

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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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (14)

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

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

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (16)

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

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

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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (18)

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.

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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

I'm an American Writer in Italy, and These Are the 15 Classic Italian Looks I Always Wear From $17 (20)

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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Insights, advice, suggestions, feedback and comments from experts


As an enthusiast of Italian fashion and a digital entrepreneur living in Northern Italy, I have firsthand experience and knowledge of the topic. Living close to Milan, one of the style capitals of the world, has strongly influenced my own style. I studied abroad in Milan during college, which further deepened my understanding of Italian fashion. I have embraced the Italian fashion philosophy, which emphasizes versatile classics, attention to detail, genuine leather, and tailoring.

Sunglasses and their significance in Italian style

Sunglasses are a fundamental element of any basic Italian look. They not only serve as a fashion statement but also have a practical purpose. In fact, the first sunglasses with UV filters were produced in the 1600s in Murano, Italy. Today, some of the biggest sunglasses manufacturers in the world are headquartered in Italy.

For a classic and versatile option, I recommend the Italian-made Ray-Ban Wayfarer sunglasses. They are foldable, making them convenient for travel, and their polished black nylon frame fits most face shapes. However, for a bolder and more glamorous look, particularly when exploring fashionable areas like Milan's Via Spiga or Brera district, sunglasses like the black Versace acetate stunners with the gold Versace Medusa on the side are a great choice.

Superga White Sneakers for comfort and style

When navigating Italian cities and towns, comfortable sneakers are a must-have, especially for long days of exploration. The iconic Italian footwear brand Superga, established in 1913, offers sneakers that evoke a relaxed Mediterranean vibe and look good on everyone. Even Kate Middleton has been spotted wearing them. Superga sneakers are versatile and suitable for all seasons, making them a perfect choice for the streets of Italy.

The versatility of a beautiful scarf (sciarpa)

Scarves are a staple in Italian fashion and can elevate any outfit. Whether styled around the neck or worn as a headscarf or sarong, scarves add a touch of elegance and sophistication. While classic Gucci scarves are a popular choice, there are also affordable options available. Amazon offers a great selection of patterned scarves for less than $20, allowing you to achieve the same stylish look without breaking the bank.

The timeless appeal of a leather jacket

A beautiful Italian leather jacket is a must-have for a Vespa ride or a post-dinner outing. Italian leather jackets are known for their quality and craftsmanship. They provide both style and functionality, with features like double zip-up panels and high collars that offer protection against the wind. Brands like Blk Dnm and Sam Edelman offer stylish leather jackets that can be paired with dresses or jeans for a chic and effortless look.

The versatility of a little black dress

A black linen A-line dress is a timeless and versatile piece that can be worn on various occasions, from dinners out to enjoying an aperitivo in the sun. Amazon offers a classic black linen dress with over 3,500 five-star ratings, making it a popular choice among customers. Its effortless style and affordable price make it a go-to option for many.

The importance of a great sun hat

The Italian sun can be intense, so a great hat is essential not only for style but also for sun protection. Hats are a popular accessory among Italians, and they add a touch of elegance to any outfit. A wide-brimmed straw hat with a beautiful leather neck strap, like the Madewell option, is perfect for the summer, whether you're lounging by the pool or exploring beautiful towns.

The significance of jeans in Italian fashion

Denim has its origins in Italy, specifically in the city of Genoa (Genova). Italian denim brands like Diesel and Guess have become synonymous with Italian denim wear. Classic styles like straight-leg jeans or skinny jeans are popular choices. Zara offers a variety of jeans, including relaxed-leg styles and shaping pairs. Pairing jeans with sneakers or classic leather Italian loafers, along with statement sunglasses, creates a stylish and effortless look.

The importance of carry-on luggage for train travel

High-speed trains are a common mode of transportation in Italy, making a reliable and practical carry-on bag essential. The Béis Weekender bag is highly recommended for its sleek design, making it perfect for overnight or day trips. It offers ample storage space and interior pockets for organizing belongings. For shorter day trips, a stylish tote bag is a good option.

Stella Jean and her colorful statement pieces

Stella Jean, a Roman designer and protege of Giorgio Armani, is known for her colorful statement pieces, which have been worn by celebrities like Beyoncé, Zendaya, and Rihanna. Stella Jean collaborates with craftsmen from around the world, promoting sustainable economic development in various communities. Amazon offers affordable dresses with bold patterns that capture the essence of Stella Jean's style.

The elegance of a tailored two-piece linen set

Pairing menswear-inspired suiting with a classic sneaker during the day and a great heel with statement jewelry for aperitivo is a favorite Italian style. Linen separates, like the ones offered by Reformation and Banana Republic, provide a timeless and comfortable look. Two-piece linen suits, such as the ones available at Abercrombie, offer a relaxed yet put-together style that is perfect for a vacation.

Gucci loafer lookalikes for Italian style on a budget

Fine leather Italian loafers are synonymous with Italian style. The Gucci Jordan loafers have gained popularity, but they can be quite expensive. Luckily, there are more affordable options available. The Vince Camuto Elpia Penny Loafer is a stylish patent leather alternative that captures the Milan-inspired look without breaking the bank.

The statement crossbody bag as a luxe souvenir

Statement crossbody bags are highly valued in Italian fashion, with luxury design houses known for their beautifully made leather products. Bottega Veneta and Prada are among the iconic brands in this category. J. Crew offers bold statement pieces, including jewel-toned teardrop earrings and gold-toned sculpted hoop earrings made in Italy. These accessories can elevate any outfit, from a summer slip dress to a classic T-shirt and jeans.

Acqua e Sapone: Italian skincare philosophy

The Italian skincare philosophy of "acqua e sapone" emphasizes simplicity and highlights the fresh-faced look. Italian beauty companies like Davines are known for their natural and high-quality products. The Davines Nou Nou hair mask, with its Brindisi tomato base, provides effective and natural hair care. To combat the effects of the Italian sun, Davines SU Aftersun hydrating gel offers intense hydration and relief after a long day at the beach.

The allure of statement jewelry in Italian fashion

Statement jewelry is a significant aspect of Italian style, with leather necklaces and bold co*cktail rings being popular choices. J. Crew offers a range of statement pieces, including gold-toned lightweight sculpted hoop earrings and jewel-toned teardrop earrings. These accessories can complement various outfits, from slip dresses to T-shirts and jeans.

The luxury of Italian cashmere

Italy is renowned for producing some of the finest cashmere in the world. Cashmere turtlenecks are a go-to choice for a classic and elegant look. Scaglione offers a maxi cardigan made with a cashmere, cotton, and linen blend, perfect for transitional seasons. For a budget-friendly option, Amazon offers an oversized cardigan that provides a similar style at a lower cost.

The timeless appeal of knee-high leather boots

Boots are a staple in Italian style, and knee-high leather boots have always been a popular choice. Italian craftsmanship and high-quality materials make these boots stand out. Zappos offers a black leather pair that captures the Italian look without compromising on quality.

Embracing Italian fashion with a knee-high leather boot

Italy has a strong influence on fashion, and embracing Italian style can be a fun and stylish way to elevate your wardrobe. By incorporating key elements like sunglasses, sneakers, scarves, leather jackets, dresses, hats, jeans, carry-on luggage, statement pieces, skincare products, jewelry, cashmere, and boots, you can create your own Italian-inspired looks that are both fashionable and timeless.

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


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