I love this question and this thread! Desmo April, you ROCK!!! What a fantastic weekend you have planned. Congrats -- and good luck!
My life is full to bursting with events that puzzle me. As I get more used to my various roles (and build the wardrobe for them) I'm getting better at figuring out how to handle the situations that tend to throw me. But here are a few of the ones that have knocked me for a bit of a loop in the past:
1. Writers' festivals where I am both a volunteer and an invited reader. On the same day. And need to dress for day and night at the same time. No opportunity to change. I have to feel comfortable for up to 16 hours at a stretch. Look approachable and in charge (for the daytime and/ or volunteer duties). Look interesting/ memorable for the presentation.
Yeah, right.
2. Conferences with my colleagues in the fitness business. Need to be casual and ready for fitness activities, but also warm enough in the air conditioned frigid hotel meetings. And while I hardly need to look corporate, I don't want to come across as a slob.
3. Presentations while I am travelling. Especially when I don't know in advance that I will be giving said presentation. Sometimes I have had to go out and buy something to wear. What can I say? A girl's gotta do what she's gotta do.
4. Invitations to teach -- in somebody's home. When my students are strangers. And mostly older women.
5. City travel where I will be on my feet from 7 am until 11 pm, mostly walking, but also going to galleries, nice restaurants, and theatre, and want to look fab throughout.