Basically, you have to build up 2-4 different outfits. I’m still working on completing each outfit, but basically, they are:
Heavy Armor: A mixture of plate and chain (mostly chain) that is used for serious combat. I have very few pieces still, but my goal is to have that 1 shiny suit of armor for when I really need extra protection.
Light Armor: A mixture of chain and leather, this is the armor I fight most of my battles in. Things like a sturdy gambeson, padded coif, chain hood, open-faced helm, padded pants, leather jerkin, gloves, boots, and the elbow guard things. (Blanking)
Stealth Armor: My current “stealth” set is mostly made of brown and green cloth and leather items. I need some items with more protection, but my noise is really good and I don’t have much trouble sneaking up on people in the dark.
Dress Attire: A decorative shirt, nice pants, decorative riding boots, and some other fine clothing items really raise your charisma. I treat them like my Sunday best and always try to remember to change into my “play” clothes so as to keep them clean and in good shape.
Once you’ve got these basics, you can just throw them on your horse (or chest) and change for the occasion. It really does pay (literally) to ride into town, rent a room, get your nice clothes out, do some shopping, and then change back into your travel clothes before you head out into the wilds.