Hmm, difficult one, I'll have to ignore the clothes I stand up in as the pockets are usually sprinkled with pockets full of stuff like knives and lighters.
Suppose like most a sheath knife would be #1. (or possibly a billhook).
#2 would be something like my Hudson Bay fire kit.
#3 a small pot with a lid, can cook, carry and dig with it.
#4, wool blanket. Can be used as bedding, shade, knapsack and a suppliment to clothes.
#5, last one is hardest, bug repellent? Personal admin kit with soft loo roll in there? A book or sketchbook? Think I'll play it safe and say a tarp.
One of my mates used to survive on trips 'round Europe on his sports bike with ultra minimal kit. All he took was his credit card and a toothbrush in his pocket. Not very bushcrafty but it made me smile when he told me.
Sent via smoke-signal from a woodland in Scotland.