Guide explaining fashion as I believe it to be.
So basically how you win is by giving gifts to judges. Buy cheap. When you gift an item, the style, color, and material from the gift will be reacted by the judge. For example, giving militia helmet makes them react to plain, metal, and casual wear. Wear what they all like and avoid what they all dislike. Gift cheap crap as much as possible. Still waiting for guide on properties of each equipment to be made. Rarity also affects it (green, blue, purple, red variety differences) Perhaps the red title has a clue to it but Countrymen's Amusements doesn't seem to be a style. Note all judges preferences are different each time. Just optimally spam the right set of gifts with all properties.
Farmingwise give everyone wolf hat, space armor, massive shotgun, fission sphere, and skin and leather.