Planning a Wardrobe

I'm taking a break tonight from working on my never-ending "not destined to be a wadder" dress. I worked on it several hours over the weekend and the end is in sight. The inside of this dress will be a mess and I doubt that I'll wear it very much, but wear it I will! Next up is two rows of ruffles on the bottom to obscure the fact that it was inches too short. I don't know what happened to that pattern because I've made that dress twice before...
So I'm taking a little time to plan out a wardrobe. There's quite a thread over on Artisan's Square about wardrobe planning, but I've never participated much. I have closets and closets full of clothes, and rarely have any trouble finding a complete outfit on the spur of the moment. This last year I've devoted myself to sewing for my lifestyle: tennis outfits and dresses to dance in. I actually still need more of both, as I move into the fall/winter season and continue with both activities. But a cruise is looming in my future, and it's a specialty cruise: dancing. Yes, there are a number of dancers cruising together, along with a dance instructor, and we will be dancing every day, I presume. In the Caribbean. In November. I'll want at least two gored/circle skirts and tops to mix and match, a couple of packable dresses with full skirts and accessories to change them up; and some other stuff like swim coverups. So, wardrobe planning. Something I'm not really that good at. Just another challenge...