Ciao from Italy! As the official motto for the Milano Cortina 2026 Winter Olympics says: “IT’s Your Vibe.”
From February 6th through the 22nd, the world descends on Italy for a high-stakes blend of global sport and personal triumph. This year, the Games are essentially a movable feast across northern Italy’s most stylish hubs, from Milan’s bustling fashion districts to the snow-dusted peaks of Cortina d’Ampezzo. Each locale offers its own unique sport, atmosphere, and — of course — distinct dress code.
Each hub has its own athletic aesthetic. Milan is all about the ice — hosting figure skating, speed skating, and hockey in the heart of the style capital. Cortina takes it to the heights with alpine skiing and the “sliding” sports of bobsled and skeleton — the ultimate “Après-ski” backdrop. And Valtellina brings the edge, featuring ski mountaineering and freestyle snowboarding against some of Italy’s most dramatic alpine scenery.
“IT’s Your Vibe” perfectly nails the Italian spirit. It’s a vibrant invitation to lean into the contrast of the 2026 Games: the exhilarating, high-altitude drama of Cortina versus the chic, high-energy streets of Milan. Whether you’re trackside or mountainside, the experience is a masterclass in duality, blending alpine tradition with urban edge.
The Winter Games begin in style at San Siro Stadium where international star Mariah Carey is set to perform, alongside Italian music icon Laura Pausini and famed Italian tenor Andrea Bocelli. Centered on the theme of Armonia (Harmony), it’s a celebration of sport, music, and Italian culture all in one unforgettable evening.
Since the festivities are split between two distinct locales, my packing list is a study in the “mix and match. Black leather pants are at the top of my list for a seamless transition from a day at the competition to an evening in the city. Style them with a silk blouse and a soft, oversized coat, then finish the look with a leopard scarf and stylish sunglasses for a polished, effortless look wherever you land.
Cool and Classic in Milan
In a feat of engineering and dramatic artistry, teams have meticulously designed and constructed two breathtaking cauldrons, one for each of the two major host cities. These imposing structures have been positioned to stand as powerful symbols of unity and passion. In a moment of historic significance and spectacle, both cauldrons will be ignited simultaneously at the commencement of the Opening Ceremony, a brilliant, unifying beacon, marking the official start of the global competition.
Known as the “Queen of the Dolomites,” Cortina d’Ampezzo is surrounded by endless and stunning vistas of the range which has been protected by UNESCO World Heritage Site. Chosen for its singular beauty and dramatic geology, this breathtaking destination of towering peaks, vertical walls and deep valleys will provide a dramatic backdrop to the Winter Games.
Hilary is all geared up for the downhill challenge in her red, white, and blue ensembles: “I chose the colors of our flag to cheer on the American teams. Red always pops on the slopes and is easy to spot as you zip down the mountain.
“I prefer a retro look to my ski clothes and love a one-piece jumpsuit. And I couldn’t resist the little Moncler pouch. Net-a-porter has all the best skiwear, and they are donating 20% of sales to MSKCC until February 6th, the day the Winter Olympics begin. Just apply the code MSK2026 at check out … it’s a win win. Now for wins by Team USA!”
Mountaineering, or “SkiMo” to those in the know, is making its Olympic debut with sprints for men and women, along with a mixed-gender relay. It’s an intense event that involves “skinning” uphill, sometimes requiring participants to remove their skis to climb particularly steep sections in boots, then quickly reattaching them to descend at top speed. Quick equipment changes are essential.
To help you find your way, the accompanying graphic clearly shows which events are taking place where!
There are many exceptional athletes to watch this year, but at the very top of our list is the legendary Lindsey Vonn, the unparalleled alpine ski racer. Following her initial retirement from competitive skiing and subsequent knee surgery, the sporting world was stunned and thrilled when Lindsey announced in 2024 that she would once again compete on a global stage.
In December 2025, Vonn became the oldest downhill skiing World Cup winner in St. Moritz at the age of 41, claiming her 83rd World Cup win and first since 2018.
Another story that has captured all our hearts is that of Maxim Naumov. Just one year after losing both his parents — 1994 World Champions and his lifelong coaches, Vadim Naumov and Evgenia Shishkova — in a tragic D.C. plane crash, Maxim is headed to the Olympics. He skates not just for himself, but as a living tribute to their legacy, carrying their “IT” factor and resilient spirit onto the world stage.
With 116 medal events across 16 disciplines, the Games also feature fresh formats and new competitions, including women’s doubles luge, dual moguls in freestyle skiing, alpine team combined, and NHL players returning to men’s hockey for the first time since 2014.
While Hilary schusses in style, KK will concentrate on the spectating pastime known as Apres Ski. Fur or Faux is de Rigeur in the toney town of Cortina, where my husband John and I spent our 15th Anniversary.
Back then, early evenings were spent strolling from the Ancora Hotel to the Hotel de la Poste, to join in the procession of sensationally styled furs, cell phones the size of dirt devils and everyone puffing away so elegantly. Ah, the good old days!
Combine these Après-ski essentials with your Milan wardrobe for a comprehensive, effortless travel kit. A fur vest, chic chapeau, cool shades, and a fabulous Prada bag are the cornerstones. For footwear, two pairs of boots are non-negotiable: one tall and sleek for the city, the other a cozy shearling for the snow. Top it all off with a Glamourpuss Red Fox Jacket to complete your strolling style.
Apres Ski Cortina Style
The Games come to an end on February 22nd at the Verona Arena, where international ballet dancer Roberto Bolle will headline the closing ceremony. Closing the loop on the 2026 style story is Ralph Lauren, marking his 10th consecutive Games as the architect of Team USA’s “all-American” look. From heritage duffle coats to vintage-inspired ski puffers, Ralph’s 2026 collection is already a collector’s dream — letting you bring a piece of Olympic history into your own winter wardrobe.
Tickets are available digitally through the official ticketing portal.
For schedules, updates, and everything you need to plan your experience, visit the Milano Cortina 2026 website.
Whether you are cheering from the stands in Cortina or following the drama from home, the 2026 Games promise a breathtaking mix of world-class grit and iconic style. From the podium to the piazza, it’s a season of unforgettable “vibes” — so make sure your wardrobe (and your remote) is ready for every moment of the action.
