I understand what you're getting at, but commissioning entirely new costumes can take quite a good amount of time and money, and the idea behind the character full-body portraits was to showcase their progressive downfall by making their original outfit skimpier and sluttier, little by little, not reflect their in-game outfits.
Sometimes, I come up with new outfits on the spot, and then they're done in less than a week by the pixel artists. If I had to track every new pixel outfit and commission the same for the full-boy portraits as well, development would get quite messy, as they would queue in the artist commission list one after another depending on the amount of other commissions they have, and maybe take several months to get done. The good thing about pixel art is I can commission several artists at the same time and players won't see the difference. For an illustration artist, once I pick one, I have to go to them for the whole game, and the more reliant I become on them, the more of a mess it'll make if something happens.
As for speech bubble's portraits, it's now a bit too late to get new ones, or I'd need to go back and change them one by one every time the character speaks with their new outfit on. For now, I'd rather keep the concept of full-body portraits as is, with one outfit that gets progressively skimpier, and eventually one new even sluttier outfit towards the end. It's more organized, easier to plan around it, and cheaper, so more money to spend on custom animations, VA, etc... : )
Well, the idea was that since they're supposed to be doomed, it didn't really matter anymore. Besides, the pirates were most likely waiting for reinforcements, so the attack wouldn't come soon, or at least not the next day. Coupled with the lack of leadership from Ulrod, people were doing whatever they wanted.
Leto wished to cheer up Cyanna, and since alcohol worked for Sgt. Alys and him a few nights earlier (I wanted to use it as a setup for the LetoxCyanna scene), it's the only thing he could come up with to help her forget about her responsibilities and everything that was going on for a time. Needless to say, it backfired.
Sure, wandering alone outside the camp wasn't the smartest idea, but when you're drunk and desperate, logic doesn't really matter anymore. Besides, from a dev standpoint, I needed a reason for the pirates to see what they saw up on that cliff, and report back to their buddies at the camp^^