9 Vacation Outfits Inspired by Street Style I’m Packing for Milan and London

If you’re reading this, it means I’m currently in Italy for the 2026 Winter Olympics. I’ve had this trip planned for months, which means I had time to really consider my packing strategy. In the end, I landed on nine New York-coded outfits that can carry me through my 20-day vacation.

I didn’t intend on wearing all-black in Milan (and London, where I’ll be spending some time), but I’m born and raised in the Big Apple, so it’s practically in my blood. I made sure to include some other trendy colors in my suitcase, though, including on-theme navy blue and bright lemon yellow. But I’m relying on (mostly) neutral pieces that can be teamed together in a myriad of ways. Every single item in my suitcase has something in common: It’s available to shop at Nordstrom, Zara, and J.Crew.