How do you think the old man got his curse?

He tried summoning Skeletron and use him to get rare dyes and fabrics. Like with all Pokemon games and 2000s Sonic games though, the ancient entity he summoned wasn't interested in working for him though.
 
I think that he entered the dungeon when he was young in order to look for things to sell, and accidentally awakened Skeletron and the skeletons; resulting in the former cursing him and using him in order to dissuade would-be intruders.
Since Skeletron's orders were simple, the Clothier actually had some leeway, as long as he kept watch all day; so he took up tailoring both to pass the time and to have something to sell to would-be adventurers, reasoning that they wouldn't be willing to explore if he put a front of a clothier that lives in an old ruin that has little of value at this point.
 
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