I got both the cross-body bucket bag and the classic messenger back to compare which one would work for me on travel/hiking trip. So far it can hold a good amount of stuff my stuff in each pocket without feeling too tight. I was able to fit my 26oz water bottle (3in diameter) in either of the side pockets but it was a little tight getting it in one side vs the other (probably just a manufacturing issue). Definitely could not fit anything with a greater diameter than my water bottle in either of the side mesh pockets. Even though my water bottle is longer than the average water bottle, I don't think it will fall out of the pocket (so far it hasn't but I will update once I have gone on my trip). I could also fit my keys, flashlight, pocket knife, portable tooth brush/tooth paste, headphones, nail kit, deodorant, combo lock, pens, chapstick, extra hair ties, small umbrella, sunglasses/case, portable charger and phone/watch charger case, mask, feminine hygiene products, iPhone 11pro, and large wallet (plan on utilizing the built-in pockets for this but wanted to see if it could fit) inside the bucket bag. The front pocket was fairly full but I could still get to everything without needing to take stuff out first. The middle pocket had some extra room if I wanted to put a second pair of sunglasses or something inside, but then it would be a bit packed in there. The back pocket had extra room that I could easily fit extra snacks or smaller items. I have not gone on my trip yet but I will try to remember to update this review afterward to report how the bag felt during the trip and how it held up with all the activities we plan on doing there. Weight-wise, it does get a little heavy (mostly if my water bottle is full) and since the strap is reinforced and a bitt stiffer, it isn't the most comfortable cross-body strap I have used. However, just a quick re-adjustment of the strap location every once in a while alleviates the slight discomfort and I have been able to wear it for a few hours in a row while running errands without it bothering me. If I could change anything so far (prior to taking it on my trip), I would like for the zip locks to be on the other side. I carry my cross-body bag on my right side (strap on my left shoulder) and having the zipper on the right side of the bag when it is closed is just an extra hassle for me as I need to move the bag a little more in front of me to unlock the zip locks with two hands instead of unlocking it with one hand. Overall, I think the back is aesthetically pleasing to look at for a travel bag, can hold a good amount of stuff without feeling overpacked, and the zip locks seem to be effective. If the strap was a bit more comfortable, the water bottle pockets a little bigger, and the zip closures flipped around then I would give this bag a 5/5 star rating. As far as comparing this cross-body bucket bag with the classic messenger bag: the messenger bag is a good bit smaller. It has a sleeker look to it but it can only hold my keys, flashlight, pocket knife, portable tooth brush/tooth paste, headphones, nail kit, deodorant, combo lock, pens, chapstick, extra hair ties, small umbrella (in the exterior mesh pockets only), mask, iPhone 11pro, and large wallet. It was also a much tighter fit with all of this stuff in it and would likely need to take stuff out of the middle pocket to reach the stuff at the bottom. My mom is planning to use this bag on our trip as she hasn't carried a purse in a long time and only plans on using it for holding a typical 16oz water bottle, glucose tablets, phone, sunglasses/case, and a tri-fold wallet. I don't have a 16oz water bottle to see if it would fit but my umbrella can easily fit in the side mesh pockets so I imagine it will fit fine. Worst case, I will end up carrying it in the second mesh pocket of the messenger bag. If you want something smaller, this bag will do just fine. Just do not plan on carrying anything in the side mesh pockets greater than 2in diameter (maybe 2.5in max).
