Trying new clothes out on vacation is a low risk way to try new clothes.
You don’t know anyone. You’re never going to see them again.
And even if you do know some people and you might see them again…No one can say anything cause you’re on vacation. If it’s not working, so what, you threw it on just to try it out. You’re trying out a weird hat or tight pants or a new necklace. It’s low stakes because no one expects vacation clothes to be high stakes.
We all need a time and place and space to try new stuff.
There’s nothing wrong with blue jeans and a t-shirt forever and ever…but you’d be missing out on the v-neck.