What period of medieval bro? I got you checked out for early medieval dark ages.
Wool tunic, wool trousers, anglo saxon turnshoes, wool cloak, wool leg bindings, wool socks, seax, leather bottle, wool blanket, nettle cordage, flax cordage, bow and arrows, stone for sharpening, hatchet, some salted pork, flint and steel, and hat.
The clothes on your body, the blanket in a blanket roll on your back and the rest in a leather haversack.
I own a pair of dark ages turnshoes. They are comfortable, durable and allow you to feel the earth under your feet. I may look like a LARPER or aragorn but they're great.