For hot climes, a selection of t-shirts, shorts and sarongs should cover most things. Although you can buy sarongs at your destination and they might be nicer and cheaper there. I have a selection of long sleeved t-shirts which I use as cover ups if it gets cool, and on the bike early mornings and late evenings. Depending on the local sensibilities, a light weight pair of long trousers makes sense. Rob nearly got thrown out of an Omani embassy for wearing calf length shorts, and I only just got away with knee length shorts, but they weren’t happy. Sandals, flip flops (thongs) and walking shoes/trainers are good. Take more swim wear than you think you will need, you will live in it and the sun damages lycra quite quickly. Depending on where you are and your dress size, you may have problems finding swim wear that fits.
I also found that some long sleeved cotton shirts (men’s) really useful for covering up when sailing in the tropics. Even with a bimini, you want to cover up after a couple of hours.
A party skirt and a couple or three tops to go with it are a must. You will want to dress up every so often.
Most of my clothes can double for winter wear (just wear more) and I have a couple of snugs and a lovely, cuddly, furry shirt. All the dedicated cold weather/winter stuff lives in a vacuum bag in one of the v berth lockers.
It may sound as if my wardrobe is sorted, but I have a beautiful beaded black skirt I have never worn, a pair of kitten heeled, snaked skin patterned ankle boots that I haven’t worn for about 10 years and a couple of tops which I can’t bear to throw out. I love them, so they stay.
Three pairs of heels? Even for work I didn't own that many, have you've given me an excuse to buy shoes? My admittedly limited shoe collection is mostly flats, sandals and sailing shoes plus one pair of cowboy boots.