I adore Bogg bags. I have a large one I use for beach trips I drive to & for my son's baseball games. I love that I can spray out sand/dirt/clay. They come with see through pockets that snap onto the holes in the bag. I have flown a few with them, as my personal item. I just snap multiple pockets into the bag and store all of my loose items in them, so when I lay it flat under the seat or into the screening basket nothing falls out. Then I add a packing cube to the middle with whatever items I want with me. My mom bought the simply southern version and it does not compare IMO. All this being said, when I flew with my broken in bag I had no trouble. Our most recent trip to DR I used my brand new one and one of the straps kept falling off my shoulder at the airport, and it irritated me enough to consider just doing a backpack the next go round and my packable beach bag for the pool/beach. Yes, they are sturdy. I weigh mine down with entirely too much stuff in my daily life, a couple bottles of wine would be no problem. Whatever you do, don't buy them from Amazon, the price is usually double. They are a little pricey, but one of the things I find worth the price as my first one is still going strong after almost 3 years. I'm not sure they are the most fashionable things I have ever loved, but I really do love them anyway lol.