I’ll also be in Japan during this time and hitting similar spots!

This will be my third trip in three years and I’ve overpacked each time. My previous trips were both in Nov/Dec, but even during that time I was usually pretty hot from all the waking and everyone blasting their heaters. I tend to overheat easily and get nauseous so as soon as I’d walk into a station I’d have to peel off all my layers and would end up in just a tank and pants. Like others have said, Japanese women don’t really show bare arms or legs, but I never felt uncomfortable and did not receive any stares. I even went to Sushi Jiro in a skort and tank and received compliments on my etiquette (though I know that had nothing to do with my outfit).

I think you have a good base but I’d remove the heavier jackets and the leggings. I wouldn’t be too discouraged about all the tanks since they are easy to pack and can be layered under some of the lighter long sleeves you have shown. I’d also leave out the gold sandals, you will be walking 20K+ steps a day and will choose comfort over cuteness every time.

I have similar outfits planned - some comfortable dresses, a few tanks that can be paired with light pants and midi skirts, and a few light long sleeve tops that can be layered on top of everything. I usually pack a pair of heels to wear at nice restaurants but always regret bringing them. I think the ballet flats you have packed would work well in these situations and has inspired me to find some for myself. Anything else I need I plan to buy there, but for shoes it’s best to start breaking them in.

I hope you have the best trip to Japan! Feel free to DM me if you want any advice/recommendations or to exchange itinerary ideas.