For Friday night Gala it's best for men to wear slacks. For the record, I'd prefer shorts too but most, if not all men, were wearing slacks. Actually, the ones who did not sort of looked out of place but hey, no one jumped up and complained. It's Jamaica, no problem mon!
For the beach party he can absolutely wear his shorts. Anything more and you'd be overdressed for sure!
These events are outside on the Great Lawn and beach so the dress shorts should be fine. You may want to dress it up a bit more with a collared shirt. You should still plan on bringing a pair of slacks, collared shirt and closed shoes with you to get into the Casanova Restaurant which is their fanciest one at the resort and has a dress code. To pay for this and not get to use it would be a shame. Remember...it may be a beach destination during the day but at night it is a RESORT. Respect the other guests and the few rules Couples has.
My husband always wears nice, Tommy Bahama dressy shorts (for all dinners except Casanova) (as a matter of fact, now that I think about it, pretty much his entire vaca wardrobe (button up shirts, shorts, bathing suits) is Tommy Bahama !! ). No one has ever asked him to change. We always go to CSS in hot, muggy August, so the thought of putting on long pants is pretty awful for him !! And, in August, we see plenty of men w/ shorts at the Gala.
I would have felt out of place in shorts for the Gala. It's a nice affair and they want to keep it somewhat formal, so why dress down? You must bring a pair of long pants anyway if you want to dine at Cassanova.
Personally, I do think that Tommy Bahama pressed shorts aren't really "dressed down" compared to junky looking jeans & cargo pants we have seen many men wearing there. And, I'm not trying to harp on the Tommy thing - if I just said "shorts" that leaves it too wide open for interpretation.
I agree Jackie. I always tell people to follow "golf course rules." If you would be allowed to wear it at a nice golf course, you are good to go. Generally that means shorts with pockets and no more than 2 inches above the knee. A shirt with a collar and sleeves is always safe too.