Tokyo - Kyoto - Osaka - Nagano Itinerary and advice

Hello!! My sister and I are coming to visit Japan in February! We are from Southern California and a bit worried about the cold. Any advice/tips on clothing and shoes we should wear would be greatly appreciated as we don't know what to expect and haven't really been in colder climates before. Here's my itinerary, tried to group everything together:

2/3 - arrive in Tokyo 7pm, activate jr pass, get to hotel and sleep 2/4 - Harajuku, Meiji Jingu temple, omotesando. Pub crawl at 7 2/5 Tokyo - shibuya crossing, golden gai, teamlab. 2/6 Tokyo - Mt takao? Thoughts on this would be helpful. 2/7 - asakusa, sensojii temple, ueno, Tokyo skytree 2/8 Kyoto - nishiki market, KIMONO TEA CEREMONY mikoya 2/9 Kyoto day trip to nara 2/10 head over to Osaka spend day and night here. 2/11 head to Nagano - Jigokudani monkey park 2/12 hike Kamikochi? Snowshoe hike - thoughts on this would also be appreciated 2/13 - anything else in Nagano I should see/do?! 2/14 - Nagano to Tokyo, Fly home to lax at 330