Sean, what a cool trip. Thank you for writing in. While I’ve never been to the Olympics, I have spent time in Milan in February for the past 20+ years for the twice-a-year fabric show. I guess you could call that the Fabric Olympics. So I can help you with a packing list for sure. As we speak, the temperature over there is high-30s to mid-40s. That’s pretty cold. Layering is gonna be the name of the game here.
My very favorite outerwear pieces are filled with Cashball and Cashpad, a recycled cashmere fill that we cannot get enough of. There’s a shorter, more casual jacket shape — the Traveler’s Jacket — and a more tailored overcoat called the Traveler’s Trench. I take both to Milan with me every winter.
As for your time in the city, Yolanda Edwards is an exxxxxcellent resource for where to go and what to see. But I’ll give you a few of our favorite spots all the same. Ann and I are rarely there at the same time — such is the fashion calendar — but we are pretty aligned on our highlights. Marchesi is a coffee shop in the heart of the city and definitely worth a visit. Though it looks really fancy, you’ll see a lot of locals there and it has a fairly low-key vibe. For aperitivo, I love B Café. Kinda divey and unassuming and totally fun. There’s a party on the street and a party inside. The music is always great. That’s a place I would love to import to the US. And then for dinner, Antica Trattoria della Pesa is fantastic. Been there forever, low-key and wonderful. Lastly, there are Princi locations all over the city for a quick lunch or snack. Salads, pizzas, sandwiches, coffees. Super reliable, super delicious. There’s almost always a line but it moves quickly.
But back to your packing list. Let’s get into it.
Outerwear: The Cashball Traveler’s Trench and the Cashpad Traveler's Jacket can be layered on top of each other, or split up and worn separately depending on the temperature (and the degree of formality). The trench is polished enough to pair with a suit, while the jacket will dress down as much as you need it to. A perrrrrfect hockey game piece. Add a blackwatch scarf and a pair of cashmere-lined gloves as needed and you’re in business.
Tailored: Keep it simple and go with a navy flannel sport coat. You can pair this with the matching trousers to make it a suit, but each of the pieces are gonna hold their own worn separately. The jacket basically acts like a winterized navy blazer. You can dress it up with a navy knit tie and a white pocket square for dinner, but it looks cool dressed down with each of the shirts on the list… even the Western.
Shirts: You’ve got to have a crisp white shirt if you’re going to Milan. The blue flannel shirt is like a winterized chambray or blue oxford. A denim Western shirt gives you a slightly more casual option, some silhouette variety, and a little subtle USA spirit. Speaking of Team USA – this plaid flannel has a bit of red and blue without getting too loud. And then there’s a really pretty tattersall twill, which is on sale, but I could not resist. It’s nice to get a little pattern underneath a navy sweater. Speaking of…
Sweaters: Navy, navy, and navy. It’s the Milanese way. You’ve got a turtleneck, a track jacket (go team USA,) and a classic crewneck. All will layer and pair beautifully with every single piece on the list… that’s the magic of navy.
Pants: A pair of blue jeans, a pair of corduroys, a pair of moleskin trousers, and the navy flannels that match the jacket are going to cover all your bases. The moleskins are on sale, which is a nice bonus, and that persimmon color pairs really well with all the navy in the rest of your kit.
Footwear: I gave this exact advice to Henrik a few months ago, who was visiting rainy Rome in December, but Blundstones and Utah grain chukka boots are all you need. Blundstones are perfect for your Olympic spectating — I wore mine as snow boots during our years in Wisconsin — but they can also be dressed up enough for the flannel trousers. The chukkas are when you want to step it up a bit more for your dinners and walking in the city, but rugged enough to handle a touch of drizzle or snow. Underneath, keep it simple with navy over-the-calf socks all the way.
As for what to wear and when… like I said, the pieces in this list are all quite configurable into any number of outfits. But here’s a starting point.
I realize this whole packing list is pretty navy-heavy, but again… that’ll be very Milanese. After the colors of the flag, navy may be the national color of Italy. They call it blu scuro. In all seriousness, though, if this packing list looks a bit spare to you… try thinking of it instead as economy. Economy of outfitting, mind, and suitcase space. This is about quiet confidence, not making a splash (the fashion fireworks already took place last week in Florence) and you’ll fit right in without being a wallflower. I hope you have the best time, that you stay warm, and that you feel great in what you’re wearing. That’s always what we’re going for.
Safe travels, Sean.
