Hello Norman, I know that this is a very LA style but I love the supreme cabin bags that LV edited this year, the red is nice but if you want a more discrete version you can go for the black one. Also, Loro Piana makes beautiful Italian bags, a real art piece! The leather is amazing. If you don't want to invest a whole lot into it, you can look into the Goyard ones, or the rigid Rimowa small suitcases. These are the brands that I would go for: I always try to invest once but well, and not demultiply the amount of things that I have, but go for nice quality and design.
As for what I put into it, I always bring a hydrating cream, a bottle of bottle that I purchased right before, a book, some advil, some vitamins, and a scarf. These are my essentials for traveling.