Acquaint yourself with restrictions on carry-on luggage size from the airline on which you will be traveling.
Determine whether you will be packing everything in your carry-on luggage or checking bags. If you are checking luggage, your carry-on does not need to be too large.
Decide whether you want to tote your bag or have a carry-on bag that is on wheels. A wheeled carry-on bag will save wear and tear on your shoulder or back but is a little more cumbersome than a bag you carry.
Choose a carry-on bag that has separate compartments instead of one big compartment. It is easier to find what you are looking for with separate compartments.
Ask yourself if you mind everyone in the airport looking at what you have in your carry-on bag. You can find clear carry-ons that make it extremely easy to get through security.