Hi Jessica,
Welcome to the Disney Parks Moms Panel and thank you for asking us a question! I’m a big fan of the “Guests without Bags” line, so I completely understand why you’d want to cut down on the amount of stuff that you plan to bring with you during your Disney Day in the Theme Parks.
The basic rule is that anything that is a bag, regardless of its size, needs to go through the “regular” bag check line as the
Walt Disney World Resort Park Rules don't specify any sizes for the bags that will be subject to search. For example, I have a small cross-body purse that I used to like to wear, but I had to have it checked with everyone else, even though it was a fraction of the side of a regular backpack.
The only things that don’t need to be checked are items that you can keep in your pockets. I usually wear items with enough pockets to carry my cell phone, backup battery, chapstick and photo id/credit cards. If you can pare down your park essentials so that they fit in your pockets, you should be good to go. Please note, however, that
Disney Security reserves the right to put you through the “regular” line at any time and that you may still be subject to search or randomly selected for a trip through the metal detectors, even if you don’t have a bag.
Please don’t hesitate to come back and see us if you have any other questions!
Have a Magical Day,
Lynne