For our Ancient Academy game of D&D I decided to have each player roll to see what extra starting item their character would begin the game with. I saw the idea for a Deck of Stuff on Jeff Rient's blog, but wanted something a little less gonzo for my game. I looked through the charts of mundane items in the AD&D Dungeon Master's guide for ideas and put together the following list.
Each player rolls a d20 for one extra starting item from the list below. This is in addition to any items they may have purchased with their starting gold.
1. ball of twine
3. buskins (cavalier boots)
9. knucklebone dice
10. long-stemmed pipe & pouch of pipeweed
12. musical pipe
13. piece of chalk
17. sprig of wolfsbane
18. vial of holy water
19. war horn
The players in my game were lucky enough to get a pot, a ball of twine, a blank book and sprig of wolfsbane.
Creating a table like this is a good way to help introduce the setting to the players. You could vary the items based on the climate and culture specific to your game world. If you wanted to put in more effort you could even have characters from different backgrounds (Civilized, Barbarian, Non-Human) have sub-tables they roll on for some of the results.