Dive into your creative stream
I wanna draw some of Dimentio's outfits from certain places he lived long before the events of the game but after he started with the whole mercenary and jester thing. :)
This one was inspired by oiran and tayuu, who were extremely skilled and educated courtesans of high ranking, they could even refuse to be with a client if they wanted to. Their outfits are usually like this:
And I LOVE traditional Japanese culture, I used to search and learn about everything, geiko and maiko (or geisha and hangyoku if you're talking about Tokyo) were my hyperfixation for some time and I will fight you if you say that they're courtesans because they are not! Oiran, Tayuu and Yujo in the other hand are.
btw, interpret the inspiration how you like hehe
also while I was drawing his hair I was thinking "King Boo would have a stroke if he met Dimentio in that era, because his hair was extremely long and as everyone know he is really into that akjds"