I know this maybe is kinda random but I noticed it feels more natural for me to wink with my left eye, right eye just feels... weird, forced. I don't know how to explain, sorry if it makes no sense.
One character I'll be cosplaying in a close future I want to do some winking shots with because it kinda fits his character.
*~Cosplays in progress~*
Masamune Date - Sengoku Basara
Eren Yeager (casual outfit) - Attack on Titan
Sanosuke Harada - Hakuōki: Shinsengumi Kitan