I Visited Milan for the Olympics—and These 11 Chic But Practical Staples Were Everywhere

Italians know how to dress. We took notes.

From camo pants to classic puffers, the streets of Milan during the 2026 Winter Olympics served as a runway for practical yet high-fashion winter staples. (Photo: Amelia Arvesen/Canva)

What do you get when a global fashion capital co-hosts the 2026 Winter Olympics? A metro full of tourists—clad in neon puffies, flags as capes, and other dorky patriotic gear—riding shoulder to shoulder with impeccably dressed locals. One weekend in February, I was among the visitors to Milan during the Games. I confess: I, myself, packed a baffled insulated jacket to wear while spectating ice hockey and figure skating in the chilly rinks.

As a gear writer obsessed with both performance and style, I spent the trip scanning outfits like I was training for a medal in people-watching. In a city already famous for turning sidewalks into runways, the collision of Olympic chaos and Milanese cool factor meant every café line and crosswalk revealed how locals and visitors were styling winter essentials. Here are the 11 chic-but-practical staples I spotted in Milan during the Winter Games.

Fur (and Faux Fur) Coats (Photo: Courtesy Save the Duck and Seniq)

On my walk to my hotel in Milan, a woman on a bicycle breezed past in a fur coat. After that, it was all I could see—people on every block wrapped in fur, be it oversized plush coats or fluffy collars. The ethics of using animal products are a perennial debate in fashion. Even so, faux fur earns its spot as a warm, cozy alternative. This hooded faux fur jacket by Save the Duck is made out of 100 percent recycled polyester and is reversible; the other side is a quilted puffer. Or if you want something fuzzier than full-on fur, Seniq’s Wooluze Fleece Pullover pulls off the same vibe—and looks just as natural on city streets as it does in the mountains.

Italian fashion is all in the details, like this intricately embroidered jacket—and fur-collar coat— spotted among the crowds in Milan. (Photo: Amelia Arvesen) Approach Shoes (Photo: Courtesy Scarpa and Salomon)

As someone who lives in a trail-adjacent city, I appreciate the outdoor brands making hybrid shoes that easily transition from sidewalks to dirt. Even the most fashionable people in Milan, a place that’s more rich in luxury boutiques than greenspaces, are keen on practical footwear. One woman on the metro was wearing these SCARPA Mojito approach shoes, which feature a leather upper and grippy rubber outsole that provides traction on icy days. Salomon is another outdoor-slash-streetstyle brand loved by the Europeans, and the XT-6s come in every color imaginable.

 

Commuter Backpacks (Photo: Courtesy The North Face)

While waiting at a crosswalk, a gaggle of Italian schoolboys clustered in front of me, every single one wearing the same Borealis daypack from The North Face, likely stuffed with textbooks and homework. I immediately recognized it because I once had a light pink and navy one in middle school, which now feels like a lifetime ago. Launched 25 years ago, the Borealis is one of the brand’s most popular packs and comes in many different color combinations for men and women. Bonus: You can usually find it on sale.

Long Wool Coats (Photo: Courtesy Filson and Canada Goose)

Any Milanese commuters not wearing fur coats were instead clad in wool coats extending past their knees. I packed my own from a fashion brand and can confirm that it’s like being wrapped in a blanket that protects you from weather. Even leggings and sweatshirts look chic under one. Filson makes a knee-length, lined wool coat for women, and the Mila Coat from Canada Goose has pockets big enough for stashing a novel. One caveat: All that material is quite an investment but worthwhile since it’ll be the cornerstone of every winter outfit for years to come.

The “Milanese cool factor” often involves masterful layering, blending textures and vibrant patterns to stay warm during the Milan-Cortina Winter Olympics festivities. (Photo: Amelia Arvesen) Workwear Boots (Photo: Courtesy Timberland and Blundstone)

I spent a lot of time looking down at shoes during my trip. Sorry to say but there were no Blundstones Chelsea Boots in sight—the uniform of every American mountain town dweller. There were, however, many other styles of boots that caught my eye. I spotted the streetwear-forward Timberland 6-inch Waterproof Boots at least twice, on men at a bus stop and at the Armani fashion museum. For those loyal to Blundstone, the Australian brand also makes these vintage-inspired full grain, rigger-style boots that look similar to a few pairs I saw in Milan.

Camo Pants (Photo: Courtesy Gramicci and Topo Designs)

Camouflage comes and goes as a trendy pattern, but right now, it’s hot in both streetwear and outdoor gear. Its military origins are clear in the details: loose trousers designed for utility and flexibility, complete with big pockets, adjustable waists, and durable fabrics. Paired with a sweatshirt or a blazer, it adds edge to any outfit. Gramicci’s classic Canvas Pants come in a tonal and subtle field camo print, while Topo Designs has a Utility Pant in a bolder duck camo.

A man in a black North Face puffer jacket and camo pants looks at a museum display of vintage wooden skis and a red snowboard during the Milan-Cortina Winter Olympics. (Photo: Amelia Arvesen) Insulated Work Shirts (Photo: Courtesy Beringia and Patagonia)

For chilly but not frigid days, a jacket isn’t always necessary—especially if once you shed layers, you have to lug your heavy coat on the subway. Cut the bulk by wearing a shirt that’s lined and insulated. This wool overshirt by the Montana-based Beringia is lined with a quilted material for extra warmth, and its felted exterior is finished by brushing thistle across the surface to create a fuzzy softness. Patagonia also makes an insulated shirt jacket out of recycled synthetic fabric that embodies the puffy jacket but in a more tailored silhouette.

The historic architecture of the Duomo provides a grand backdrop for the modern, tailored silhouettes favored by locals and visitors alike during the Milan-Cortina Winter Olympics. (Photo: Amelia Arvesen) Sport Sunglasses (Photo: Courtesy Vaurnet and Oakley)

Sporty sunglasses used to be dorky. Now they’re fashion. Remember the girl wearing the fur coat on a bicycle? She was also wearing full-face shades. Smart for blocking wind, bugs, and sun. I also saw loads of city runners on the road and clocked one man wearing a pair of Oakley Eye Jacket, a style that first emerged in 1994. For another option that’s sporty but still street-friendly, Vaurnet (whose founder won bronze in downhill skiing in the 1958 Olympics) makes a pair that look like glacier glasses with removable side shields and scratch-resistant lenses.

Travel Duffels (Photo: Courtesy My Style Bags and Peak Design)

 

For the people of Milan, even the most practical items look elegant. Take the duffel bag, for example. Whether they’re schlepping it between work and home, or taking the train to a weekend retreat at Lake Como, the bag still matches the outfit. One brand I spotted was the Milan-based My Style Bags, which designs duffel bags, suitcases, and handbags in durable materials. Every bag is customizable with embroidery, much like L.L.Bean bags. For a budget-friendly alternative, the Peak Design 50L Travel Duffel is sleek and also weatherproof.

Elevated Slippers (Photo: Courtesy Bombas and Salomon)

Leaving the house in your pajamas is usually considered a fashion faux pas—unless it’s intentional. Gen Z has once again popularized the UGG boots of my teenage years, and that includes the full spectrum of shoes that are easy to slip on. I spotted even the most fashionable women in slippers, similar to the Bombas Saturday Suede Slip On with a water-resistant shell and sturdy sole. Another guy was wearing the Salomon RX Slide 3.0 (though not in hot pink).

Practicality meets personality on the streets of Milan, where even a morning school run becomes a runway for bold patterns and bright winter accessories. (Photo: Amelia Arvesen) Tailored Trousers (Photo: Courtesy Arc’teryx and Finisterre)

What struck me most about Milanese style? Even the simplest outfit fits like it was made just for them. Most locals have their own tailor, and it shows in every jacket, shirt, and pair of trousers. In lieu of visiting the seamstress, you can get the same look by wearing a sharply-made pair of pants. Though pricey, the women’s Arc’teryx Dias MX Pant features clean lines in a winterweight fabric that’s lightly weather resistant and stretchy. No ironing required. For men, Finisterre has a relaxed but sharp workwear-inspired trouser made of a heavyweight cotton duck fabric. Over time, the fabric fades with character, like a worn-in leather boot or jacket.

A long wool coat and tailored trousers are Milanese staples, providing essential protection and effortless style even on a rainy afternoon during the Winter Olympics. (Photo: Amelia Arvesen)

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