It’s been ages, since I’ve done one of these. It may not be the most practical of features (sorry dudes!), but it sure is fun to do. And we all need a little packing inspiration from time to time…
In Japan, I found simple dresses to be most practical. They are still traditionally expected garb for women at a nice dinner or cultural event. Just avoid anything low-cut or you’ll quickly feel immodest. Sneakers are a no brainer, and a stylish backpack* keeps your hands free for biking. The locals all use umbrellas rain or shine, but I felt a little silly toting one around unless it was pouring.
(I generally don’t provide links to the actual items because I aim to choose simple things that are available in any price range, but ask me if you’re after something in particular).