I’m always asked how I get so much in my carry on bag and the answer is simple, I minimize what I take and here is how I do that.
First, determine how much space you have in your bag. I prefer a hard sided bag because it has at least two compartments or sides.
I put my shoes, toiletries and underclothes on one side and my regular clothes on the other side.
I keep my toiletry bag small and everything inside follows the 311 rule. My cosmetics bag is also small and everything fits into one small bag. I take only the items I’ll use during the trip like mascara, an eye shadow palette with at least 4 colors, two lipsticks (a neutral and a popping color) and a moisturizer foundation. You can use your lipstick for a bit of blush.
I take a maximum of two pairs of shoes, unless I have activities that require special shoes. I can do this because I stick to a color palette so one pair for casual and dressy will go with every outfit.
Sticking to a color palette answers one of the questions about what to take. Doing so means that every item should match or coordinate with the others. Bring items that can go from day-to-night easily and bring more tops than bottoms. For pops of color, accessorize with scarves, shawls or light weight jackets. You can wear your jacket on the plane.
If you feel you need more items, use a space-saving bag to, well save space.
I hope that helps! Just know and take comfort in the fact that you don’t need everything in your closet!