Could this be classified as a Personal Item on a flight?

Yes, I have taken it as a personal item on a flight no problem.

How l Unwrinkle bag? Any ideas

Hi dear friend, you can flatten it with an iron. Plus, it can be filled with filler when not in use. Hope it can help you.

How wide do the elastic side pockets open? Specifically wondering what circumference water bottle/umbrella would fit.

Like a water bottle. I use this as a diaper bag and it has pockets inside for like a water bottle. If I put 2 water bottles inside you definitely can’t stretch the outside pockets for water bottles. Idk if that makes sense.

What size water bottle would fit in the side pockets?

It has 2 inside pockets too I use it as a diaper bag and I put a bottle in the inside pocket and and a plastic water bottle inside too or a thermal water bottle. The outside pockets are a little tighter idk why so I normally just put my phone or something smaller there.

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