Inspired by the B/X Headgear tables from B/X Blackrazor, here is my version of a random headgear generator presented in four installments (because they do not fit neatly on one page, unlike their inspiration). Each player character may roll for one item (hat, non-hat, helmet, or wizard hat), which may be worn, stored, sold, traded, donated, or discarded as desired.
Suitable Non-Hats for Adventurers
Roll 1d20
1. Bandana
2. Burlet and Veil
3. Chaperon
4. Circlet
5. Coif
6. Cowl
7. Cord
8. Diadem
9. Feather or Flower
10. Headband
11. Hood
12. Hood, Fur-Lined
13. Hood with Liripipe
14. Hood with Ornament or Bell
15. Hood with Tassel
16. Mask (specify or roll on Masks table)
17. Scarf
18. Wreath of Flowers
19. Wreath of Leaves
20. Wreath of Vines
Masks
Roll 1d20
1. Bandit Mask
2. Bear
3. Bird
4. Bull
5. Demonic
6. Dragon
7. Face, Angry
8. Face, Blank
9. Face, Laughing
10. Face, Leering
11. Face, Sad
12. Fish
13. Frog
14. Lion
15. Masquerade Mask
16. Punchinello
17. Scaramouche
18. Skull
19. Tiger
20. Wolf
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