Every summer since moving to Italy, my Instagram direct messages are filled with American friends asking me, “What should I pack?” before their upcoming European vacations. But the truth is, the answer varies depending on where you’re headed. What I pack in my weekender bag for visiting Tuscany differs greatly from what I’d be taking on a holiday in Sardinia. And, there’s the matter of personal style to address—I like to think I take a little bit of Italian summer style and make it my own.
Still, there are timeless Italian style pieces that will work for all wardrobes and destinations—and to determine the Italian summer style must-haves, I turned to my most fashionable Italian friend, fashion designer Stella Jean. I’ve been a huge fan of Stella’s work since the early days of her brand; a protege of Giorgio Armani, Stella Jean has dressed global style icons like Rihanna, Beyonce, Zendaya, and Sandra Bullock.
In that oh-so-romantic Italian way, Jean not only gave me packing tips, but life tips on how to channel Italian style: “Don’t just pack clothes—pack attitude,” she told me. For her, the hallmark of Italian summer style is “disinvoltura studiata,” which translates literally to “studied ease” but to Jean, is defined as, “That elusive mix of ease and intention—where linen is always slightly crumpled (but never careless), and sandals are custom-made, possibly in a fishing village with no Wi-Fi but generational savoir-faire.” Hallmarks of Jean’s collection, like her striped button-down shirt and bold patterned skirts, channel that disinvoltura studiata. To help you put together your own summer travel wardrobe, read on for eight Italian style tips based on Jean’s advice.
Linen Set
My linen wardrobe has dramatically increased since moving to Italy, strongly inspired by my husband and his full linen summer wardrobe that certainly caught my eye during our first summer dating. I learned from him how to wear and style linen, and now I love the fabric, particularly in the form of a matching set. Currently, I have three linen sets in my suitcase! Jean attests to donning linen in the summer as well, saying, “It’s slightly crumpled, but never careless.” I selected a few of my favorite looks, including a matching square-neck tank and skirt set from Madewell and a sleek cropped vest and high-rise pant from Gap.
A Striped Cotton Poplin Shirt
I’ve always appreciated the ease of the summer button-down shirt. Tied at the waist or tossed over a swimsuit, button-downs are a versatile style I’ve worn for decades. There’s a beautiful familiarity to the style of a striped cotton poplin shirt I’ve seen worn in Italy. For Jean, a striped cotton poplin shirt is “a quiet staple of the Italian summer, beloved by philosophers, fishermen, and flâneurs alike.” Stella Jean’s striped shirts in a beautiful blue and white have always caught my eye, especially paired with eye-catching skirts, proving a striped shirt is not only a staple but also a neutral! I also found an oversized option from Madewell and a bright vermilion hue from Gap’s partnership with Dôen that will definitely stand out.
Palazzo Pants
Beautiful wide-leg trousers and palazzo pants have always been a hallmark of great Italian style to me, and it’s true for Jean, as well. After all, “palazzo” pants are Italian (hence the Italian name), and are one of my oft-mentioned style staples. These comfortable, flowy bottoms are just as fitting for swanning through an Italian city’s palazzo as they are for exploring small, tucked-away Italian towns and villages. Check out the best-selling Madewell Harlow Trousers for a more polished look or the white Quince wide-leg chino pants that are practically made for summer.
Leather Capri-style Sandals
One of Jean’s top non-negotiables for Italian summer style is a pair of leather Capri sandals. “For me, it’s never really been summer without them,” she says. “I started wearing them around 14, when my mother and I would have them made to measure in Positano or Capri. They’re the kind of sandals that work [24/7]—from breakfast in linen to evening in a flowing dress.” She adds that she probably has 20 pairs by now, “bought out of pure loyalty and frequent overuse.”
But, if you can’t make it to Capri or Positano for your fitting, get your pair from my husband’s family’s company—I’ll ask my father-in-law to sprinkle in a little Italian sunshine into your package! You can also shop similar-looking leather sandals, like this strappy pair from Bernardo or this Cole Haan fisherman sandal.
A Day-to-night Dress
Pieces that work for day-to-night wear feel elusive, but Jean manages to master the art in her gorgeous dresses that you can put on for almost any occasion. “Ask yourself: Would this look out of place at a café at noon or in a piazza at midnight?” she says. If it suits both locales, then it’s ready to go. Some of her most iconic dresses, like this striped floral midi dress with its striped cotton poplin shirt and full skirt featuring a bold colorful print, are reminiscent of the Caribbean, reminding me of Jean’s cultural heritage as half Haitian. As seen with a pair of flats on style star Luna de Casanova or with heeled sandals on Jean herself, a versatile dress that blends styles is elegant for both day and night. Other dresses that capture a similar day-to-night feel are this gingham number from Gap x Dôen and this lightweight pinstripe Quince dress made of European linen.
Printed Skirt
One of Jean’s packing recommendations is a bold printed skirt, especially in a beautiful tropical print. A few years ago, while styling a photoshoot on the cliffs of Ravello along the Amalfi Coast, I used a cobalt blue painted draped linen skirt. I styled it with a crisp white button-down, and it’s still one of my favorite looks. This Stella Jean Midi Wrap Skirt reminds me of that shoot and that beautiful summer day, and I can imagine packing it along with a crisp button-down or tank. I found a few more eye-catching skirts to pack for an instant outfit upgrade, like a colorful midi linen skirt from Banana Republic and a forest green printed skirt on sale for $27 at Amazon.
Pinstripes
The Italian pinstripes! While casually naming things to punctuate an outfit, Jean suggested adding pinstripes to your packing list. It’s a hallmark of classic Italian style, beloved by everyone from bankers in Milan to politicians in Rome. There’s a huge variety of pinstripe looks, like these wide-leg yellow linen pants from Mango or these Everlane barrel-leg pants with a dark denim pinstripe.
Light Scarf
I recently said to my husband, while packing for our vacation in Sardinia, “I’m going to pack a scarf. There might be a breeze at night.” Have I become Italian? As Jean joked when suggesting a light scarf on her packing list, “Italians will forever believe that il colpo d’aria is a real and present danger.” You’ll get a cough with your throat exposed! But a scarf can be worn in several ways, making it a genius accessory to pack with you. For instance, Jean styles a head scarf impeccably well. When meeting her for lunch in Rome once, I was in awe of her striking figure in a beautiful head scarf and trench coat; I promptly styled a similar scarf for my flight to Nice the next day! One of these silky numbers will work overtime on an Italian holiday, whether you’re tying this linen scarf around your neck or this parrot-patterned one over your head or tied to your purse.
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