Is gets really windy on deck when the boat is moving. Chill, too. You'll want something warm for that and also a way to wrangle your hair. We went on an Alaska cruise last year at the beginning of July. Dining was very casual. There were a few people in formal clothes--kinda looked like they were dressing for prom (hehe!). We felt we dressed nicely, in clothes that were sorta business formal, but there were people who made NO effort at all--camp shirts, shorts, flip flops etc. at dinner. Also, we ended up eating al fresco a lot for breakfast and lunch because the dining rooms were quite crowded. On the whole, it was chillier than we would have liked for that activity--and the wind was a continuing issue. Honestly, I don't remember how I dressed, but I'd suggest packing items that will be warm without being too restricting for eating and for wrangling food at a buffet line in case you find yourself in the outdoor seating. (Of course, it's not the only option...)
It rains a lot--especially southern Alaska--so I'd be prepared with an assortment of wet weather gear.
Also, there can be a significant difference in cruise lines. We were on a Norwegian Cruise. I didn't know, before-hand, but Norwegian has a reputation for being like the Applebee's of cruising. I think that was reflected in the casual attitude of many guests and the fact that a lot of guests seemed to be there only for the free bar. Your experience may differ. We did enjoy the the experience--both the cruise and the destination.
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