I have found that having some set pieces to wear on vacation is the easiest way to pack. Last year we took a couple of two week trips and I essentially packed the same things for both trips. I have another big trip coming up and I think that will have pretty much the same things. i don't like to have too much clothing especially when I am moving to different cities/hotels. I pick one color palette and try to stick to it. I don't feel I have to dress to impress so if I look boring, that's life. I would rather not spend my time thinking about what I will be wearing when I have to get up really early for day trips or transiting. That all being said, I HAVE to take a pair of Chanel two tone shoes and one Chanel jacket lol! One good bag that works for day or night and I am done!
You are a minimalist packer. I like to bring my things out to play on vacation. But I carry what I bring so I keep it reasonable.