The whole point of holidays is that you get to make joy and fun the main event. On holiday, having a lovely time is basically your job. And you know what they say about jobs, right? You should dress for the one you want. So on holiday, if you want to have a really super lovely time (which I’m thinking is a yes) then start by dressing for it.
That means forget about being taken seriously for a bit. On holiday, in fact, you want to dress to be taken as unseriously as possible. That way, everyone around you will understand that you have taken a hard time out from your to-do list, and that your decision-making responsibilities are zero (except in the ice-cream parlour). Lean in to dresses you can take a nap in (a whole genre of flowing dress known, incidentally, as nap dresses), a thin silk scarf you can tie your hair up with, and shoes you can kick off to paddle in the sea. Become the Sheryl Sandberg of broderie anglaise dresses and shorts you made out of last year’s jeans. Dress for joy, dress for fun.