While planning an early summer jaunt to Italy—a trip where outfits are as important as museums and dinner reservations—I suddenly found myself unsure of what to pack. For a trip that would take me through the fashion capital of Milan and into the luxury enclave of Lake Como, I feared I wasn’t up to snuff on Northern Italian style of dress and felt like my typical holiday wardrobe of black-on-white-on-black-on-black needed more pizzazz. Should I eschew my black wide-leg pants, Grecian slides, and cropped tanks to go full on sling-back heel, voluminous floral skirt, and petite doctor’s bag? A tiny cashmere cardigan draped elegantly around my neck? Or should I idle the day away in a Pucci caftan, Dolce & Gabbana pajama set, or Missoni striped dress? Should I rent a turquoise Vespa and zip around in a cacophonous mélange of head-to-toe prints, like one of Milan’s most famous dressers Anna Dello Russo?
I was lost.
I decided to enlist local experts and influencers who could speak to the fashion landscape of these destinations. The journalist J.J. Martin knows a thing or two about Milan’s dress code: A venerable expert on Italian taste, she documents the city’s aesthetic on her website and vintage shop La DoubleJ. “Milan style is crisp, buttoned up, and understated, but it also has a special flair,” said Martin, who launched a collection of colorful Milanese dresses using prints and silks from the archives of Lake Como's Mantero, the famous textile production house that also manufactures the label. “There’s always a touch of color, a flash of print, or something unusual that shows the person has style and paid attention to how they got dressed that morning.”
Not surprisingly, Martin references Miuccia Prada as the quintessential Milanese female archetype—the embodiment of the city’s chic kookiness, where women hold court at the Hotel Principe di Savoia, Dorchester Collection while peacocking in clashing prints and kitten heels. But for Italian blogger Chiara Ferragni, Milanese style is a bit more streamlined than that. In her world, it’s not unlike New York dressing—efficient, transitional, and modern. “Milanese style has its own uniqueness as it reflects the kind of lifestyle that people have here,” said Ferragni, whose website The Blonde Salad showcases her global fashion escapades. “This means men and women who are totally focused on their career, but balance it with a healthy lifestyle. They have to look elegant but not too formal, an office look but with a fashion twist.”
Ferragni says she feels most “Milan” when she’s wearing something as simple as a chic black pantsuit, sans blouse, tied together with a belt for added flair. She credits Versace, Moschino, Marni and, of course, Prada, with establishing the city’s look.
And who could mention Milanese style without referencing fashion’s vibrant Gucci craze, a groovy mash-up of colors and prints ripe for traversing the Corso Venezia. Certainly not Lisa Aiken, retail fashion director for luxury site Net-a-Porter, which happens to carry a full breadth of iconic Italian brands. “Gucci really does embrace this idea of individual dressing, and Milan has very much established itself as the individualist,” said Aitken, who attends Milan’s twice-annual fashion weeks. “While there is an element of glamour in Milanese style, it has this certain ‘effortless fashion’ about it, which really sets it apart from the rest of the globe.”
Now that I have a handle on my Milanese looks, I’d assume style simmers down on Lake Como, the summer haunt for the city’s noblest families as well as Hollywood royalty like George and Amal Clooney and John Legend and Chrissy Teigen. At least in New York, dressing in the Hamptons and Nantucket is a more relaxed affair than in the city itself. Not so fast, says Valentina De Santis, owner and chief executive officer of Lake Como’s iconic Grand Hotel Tremezzo. She’s had the fortunate perspective of living both in Milan and on Lake Como and can say, without a doubt, that the latter is more formal. “Como is more chic, Milan is more trendy,” said De Santis, whose hotel recently began managing the region’s celebrated Villa Sola Cabiati. “Surprisingly, parts of Como are more fashionable than Milan. There are a lot of people from all around the world in Milan and it is generally more casual than Como. Como is a smaller town but rich in terms of heritage, and people tend to dress a bit fancier.”
De Santis says romantic caftans and oversized hats embody the wardrobes of Lake Como, as do custom silk dresses and scarves. The region is famous for its silk production and services the fabric to luxury brands like Louis Vuitton and Chanel. De Santis does most of her shopping at a local Como boutique called Moresi that produces its own knitwear. “Their styles are chic and timeless,” said De Santis. “I wear these simple clothes with accessories from designers such as Valentino.”
With my newfound sunny vision of Como dressing, and a more nuanced understanding of a classic Milan wardrobe, I’m ready to attack my suitcase with rigor. I may not veer too far from my typical vacation style of dress, but perhaps I’ll throw in some more color and, at the very least, a little ladylike flair in the form of a fitted dress, tiny bag, and a colorful shoe. After all, if Dello Russo is any indication, when it comes to Northern Italy, more is certainly more.
