Backpacks are magic for longer trips. Food, water, coffee, all go in. Unsure about the weather? Layers layers layers, all in the pack. I also use LL Bean's PrimaLoft Packaway (I own two, one black and one orange), and have a shell for rainy/snowy weather. Unless it's both cold and rainy, one of the two goes in the backpack.
I've also never worried much about pocket preferences on my shorts and pants. I instead care about pockets on my packs. My current big pack is an Osprey Exos 58 (but the newer version doesn't have hip belt pockets or a shoulder strap pocket), and my daypack is an REI Flash 22 (with easily accessible side pockets, and a top pocket that you can reach with an awkward shoulder movement).
Edit: The big floppy hat comment was absolutely spot-on