I find it still funny that in cookie run Kingdom when you get the costumes unlocked the first ever thing you get is a suit for gingerbrave. Even the game hints at him to put on some clothes
I headcannon the reason why he doesn’t wear clothes is because he didn’t have any to begin with (yknow, waking up about to be eaten and all) so he just… didn’t really know what clothes are. But the more people keep bringing it up the more he’s becoming embarrassed and subconscious about it lol. The only reason why he hasn’t tried to get any actual clothes is cuz he’s always traveling, so he either forgets too or doesn’t feel the need too when there isn’t a lot of cookies around
To be honest, I've always thought that GingerBrave was always wearing a nude-coloured suit (judging from the skull shaped buttons as a part of his design) and I still interpretate it like that..