when I was in my late teens and early twenties I belonged to a  young adult group that met every Sunday evening in a church basement - we used to have a Halloween party every year.  I bet my friend Frank that he would not recognize me.
At the time I  pretty much  was the makeup department at my  college theatre dept 
I used nose putty to build up  my nose,  gave myself a swarthier complexion with pancake makeup, gave myself a  beard and moustache and bushy eye brown with black crepe hair and put on a short black wig,  then I put on my brother's  olive green work pants, my dad's old army jacket and my brother's work boots 
the room we met in had two entrances , I came in the back one and saw  Frank sitting on the couch facing the front entrance.  He was busy telling everyone  about  our bet and explained it didn't matter how I dressed because  he knew he would recognize me because I was the one assigned to bring the cake!
So I sat down next to him on the couch and waited  silently.... about 5 minutes late r my brother came in the front entrance (carrying  the cake I was assigned to bring)  and Frank  told everyone - Ok she'll be next!... then he waited and waited and finally asked my Brother , "Hey where is your sister?"
"Sitting next to you !"
All in attendance agreed I  won the bet