What seasons or occasions do you find the most difficult to dress for? Something unexpected, unexpected weather change to make your planned outfit a problem, just some seasons, hot spells or ?

I always find hot a problem, and there has been a lot of discussion on hear about this, In general summer is more difficult than other seasons for me. Special occasions like dress up are easy as I have quite a few items to play around with. Having the right LBD that can be dressed up or down is a good workable idea. I am also finding that just learning how to work with basics like good fitting staples lblack pants, a good white silk or some such top (which I do not have) may be an answer.

Your thoughts?