October was simultaneously one of the best and most exhausting months of my entire life. It started with 10 days in Italy and Switzerland, where I traveled with my single carry-on suitcase from Ligurian Sea towns to Milan to Lake Lugano. It was 80° by the water, calling for bikinis, cover-ups, and billowy skirts and dresses. Meanwhile, in the cities, I needed lightweight outerwear for the chilly early mornings and evenings spent café and restaurant hopping as well as comfortable walking shoes that still fit in with the chic nature of my surroundings. Packing everything for the dueling settings was a bit like playing Tetris with the limited amount of space I had in my suitcase. Plus, I needed room for shopping.
A handful of days after I returned home to New York, I left again for a week—first to Chicago, where it was already pretty much winter, and then to Austin, where it neared 100° every day. Somehow, I managed to keep most of the contents of my Italy suitcase intact, only switching out the swimsuits for two coats and adding a few Western pieces to fit the local Texan aesthetic.
In total, I hit five locations, from Austin to Lugano, with pretty much the exact same items, give or take a few. Below, see which pieces worked for them all, despite the changing weather, occasions, and dress codes.