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Whatever it looks like, your carry-on had better fit in that overhead bin once you're on board the plane, and your personal item needs to fit under the seat in front of you. You may not want to cram your Kathy Van Zeeland handbag on the floor, but you may have no choice. When you're packing, bear in mind that you will need to lift your carry-on luggage into the overhead bin yourself. Flight attendants may assist but cannot do it for you.
If you're not one of the first people on the plane, it may be necessary to pack your carry-on some distance away from your seat. In the frenzy of boarding, stowing your gear and getting seated, it's easy to lose track of where exactly your bag is. Make things easy for yourself later by making a note of the compartment number or seat number nearest to your bag.
Especially if you have a heavy bag, be careful taking it down at the end of the flight. Many a passenger has suffered a bruised shoulder because someone else's bag fell out of control.