Whenever we have a city vacation planned, I make a habit of wear-testing some of the outfits I plan on packing in advance. Here’s one I tested out last year ahead of our trip to Japan — and sure enough, it made it into my suitcase for the trip (albeit with different sneakers). With our upcoming trip to Portugal on the books for later this spring, I’ve been narrowing down the outfits I want to bring, this maxi skirt look being one of them. This entire look, minus the new leather jacket, is actually one I wore multiple times in Japan, so I already know it holds up for a long day of walking. I mainly wanted to see it with the addition of the jacket, since it’s the only one I’m planning on bringing. Next up: seeing how the jacket goes with my trousers and jeans!