Milieu the Deft, Travelling Hat Salesman
I've been playing The World Ends With You on a borrowed 3DS, and while it has my brain buzzing with near-future psionic stuff, I really dig how it deals with items. Most items are clothing (I might do another post about food), and these are gated behind Bravery, with more daring items (with more helpful abilities) requiring a character to be more Brave to wear them. Different clothes are more or less popular in different parts of the map, giving you buffs or debuffs. The other interesting bit is that clothes' abilities are hidden until a merchant tells you about them. They will reveal two abilities when you first enter a shop, and more as you buy more items from them.
It's all very crunchy and videogamey. Obviously not every part of the clothes system in TWEWY is going to work in a tabletop game, especially the kind that I run where a +1 bonus is kind of a big deal. I like the idea of characters having a Bravery score, and items having abilities that merchants only share if they like you. There is some OSR Blog Precedent for classic D&D characters to wear funny hats, so that seems like a good place to start.
I found these illustrations of historical headwear super helpful.
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Milieu is easy to spot, in his bright red poncho with blue embroidered feathers, his wide handlebar moustache, and the dozens of hats he wears, all balanced carefully on his head as he shouts "Hats for sale! Glorious hats for every occasion!".
Mileu will share the special ability of only two hats that he sees customers being drawn to. For every two hats sold, he will reveal the special ability of one more.
A character's Bravery score is their Charisma+Level. Wearing clothes designed for another gender requires twice the Bravery score (nonbinary characters suffer no such penalty).
Inferno
Men's leather skullcap embellished with goat horns. Bravery: 10. 300sp
Bonus: +1 to saving throws against fire.
Special: Lose 1d3 HP to turn a mundane blade into +1 flaming for 1 turn.
Nurture
Ladies' lavender coif with embroidered white flowers. Bravery: 10. 250sp
Bonus: 1-in-6 chance of cast spells not being forgotten.
Special: Seeds you plant will undergo 1 week of growth within the first day.
Stillwater
Men's navy baret with a silver swan brooch. Bravery: 12. 500sp
Bonus: +1 reaction from aquatic creatures.
Special: You have a 4-in-6 chance of predicting a person's next action by seeing their reflection.
Laurel
Ladies' gold-wire chaplet with enamel leaves. Bravery: 12. 500sp
Bonus: +1 Armour Class bonus against forest creatures.
Special: You can sacrifice this hat to make a wish for a small, natural item. 800sp
Hunter
Men's fur hood with wolf ears. Bravery: 14. 600gp
Bonus: +10 to movement speed, +3 to reaction of wolves, -1 to reaction of prey.
Special: Once per day, you can transform into a werewolf for 1 turn.
Presence
Ladies' purple escoffion with brocade rushes. Bravery: 14. 1200sp
Bonus: You only have a 1-in-6 chance of being surprised while travelling in a swamp.
Special: Once per day, call a giant toad to your aid. They arrive in 1d6 rounds.
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Reading: Werebeasts of Hel by Asa Drake
Listening: Lego Castle: 1979-1998 by Dreamcastle