Here's how emotional dressing affects my packing: I am an anxious person and I need some "security" items that will make me feel cozy and comforted. So I will bring things that are not necessarily practical, and I'm definitely not an efficient packer, partly because of this. That, and I also want to be "prepared for everything." I'm working on it and using post-trip tracking to pare down my luggage. But there will always be room for one or two comfort items...

Re: resort dressing, the resorts are casual and there is a lot of beach/pool time but at meals they do ask that you not wear (just) your swimsuit. There are also lots of pretty flowers and tropical inspired decor that influence my esthetic while I am there. So I like to have a casual but pretty cover up outfit of some kind for day. The type of shorts I might wear for hiking at the cottage back home just don’t feel great, but a flowing cover up with nice details does. At night I do like to dress up just a bit for dinner and any evening activities (which might be dancing or entertainment), because it feels festive and helps structure or break up the day somehow - it can get a bit monotonous, in the most pleasant way, staying at these all inclusive resorts for a week. Although my fellow Canadians who frequent these places are often quite casual, I notice the European and local guests also look nice for dinner.

I buy necklaces and earrings while on vacation. I also picked up a bracelet in Ireland as I had been looking for one for about ten years
and found it there so it was not really a vacation purchase.

I think the thing is, traveling is a unique situation with distinct and predictable emotional needs for me...

Rachylou, if you can predict your moods in advance, that’s awesome!

KM, why not take comfort items, as long as you have the rest pared down?

Freckles, how nice to have souvenirs of your travels that you can wear all day!

Jules, im lazy. If we were to eat inside, we’d have to get dressed for real, but we don’t. It’s sort of a tradition with us that he can order pancakes from room service, and otherwise we eat at the cabana bar at the pool. But we just stay for a couple nights at a time. If we were there for a week, I’m sure it would get old, and I’d have to do as you do and get dressed. But I still think it’s relatively easy to predict activities and mood for that kind of stay.