Before you do anything else, check with your airline on the dimensions they allow for carry-on luggage.
However, these airlines have no weight limit on the bag.
It just has to fit into the overhead compartment (viaTravel + Leisure).

If you know how to pack your carry-on right, this shouldn’t be an issue.
If these things are included with your hotel stay, you don’t have to pack them.
You might not even want to pack everything you have laid out.

The less that goes in the carry-on, the easier it will be for everything to fit.
The shirts will unroll unwrinkled and leave more room in your suitcase.
Pants and sweaters can just be folded into squares, making them quite compact.

Now that everything is ready, it’s time to place the items, starting with the square ones.
Place these in the carry-on luggage first, and the rolled shirts can surround them.
Your socks and shoes can then go into any empty spaces you see.