Toad, what do you mean, if things go well???
Anyway, yes do bring a dress or two. Or better yet, buy one when you get down, there are some great little shops in San Pedro for that kind of thing. Most people that actually live in San Pedro dress to go out for dinner, remember it is not an everyday thing no matter where you live, gals wear heels and all that, while a lot of visitors, not all, some dress to kill, and some notorious expats tend to wear the same thing for dinner out as they wore on the boat! I have been forced to go to "nicer" places in rather scrubby clothes, because there was no time to go home and change after a day on the water and a drink or two to discuss "da fish". How you dress really doesn't matter to anybody but you, there is no such thing as the right thing in San Pedro, but it sure is nice to look good every once in a while! Just have a great time, will you!