I would not go for the fleece jacket. I've been there in both May and Sept, the 2 coldest months and only had one day when I was truly cold. But, the breezes up on deck can be chilly and if it rains, which it does a lot, that can be chilly as well. Hence the advice on a waterproof windbreaker. Layers under that and you will be fine. I did take gloves and a headband, which I used maybe once each trip.
Re. shoes, it depends on what you want to do in ports. If you were going to Alaska for extended land vacation, then hiking shoes might be needed. But, I am physically limited and spent most of my time either on a bus, or boat tour or some light walking around in town. Hubby did climb up the hill (mountain?) in Juneau and even he just had on good walking shoes. So, plan around what you plan to do.
Alaska is not as cold as most people think. Sitka never goes below freezing, even in the dead of winter. And, most of the activities that would require special gear and shoes are too far inland to do from a cruise.
Marty....who loved Alaska inspite of hating being cold!