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About your problem, look at my second tip. If that doesn't help then is probably a mod conflict. I can't help with that but last I played with Awesome Inventory I had zero problems with 300+ mods. But you can check it by only loading Core, Royalty, Awesome Inventory and create a new colony and follow the guide steps. It should work like in the GIFs:
GIF [i.imgur.com]
GIF [i.imgur.com]
From wiki "Pawn won't take off apparels that are not listed in costume unless they are in conflict with those listed in costume."
You will need to use any type of Hat to switch from Helmets (and vice versa) and a Formal Vest (or any other modded middle layer cloth) to switch from Flak Vest (and vice versa)
It's usually not a big problem because later in the game pawns will all have hats but Flak Vest can be annoying because vanilla rimworld only have armors and Royalty clothes that uses middle layer, all the other clothes are skin layer and outer layer.
Of course it stops being a problem when you upgrade to proper armor (Recon, Marine, Cataphract, modded armor) because a Duster, Jacket or Parka uses the same slot, so you can switch between them easily, flak vest is just awkward.