Spoiler
What does immost mean? I assume vulgar or provocative?
Also did I actually find out what the three siblings do? I mean I recall the girl was a... well... woman of debatable affection or perhaps a "leader" of such women... but what where the guys? Pimps? Thugs? Thieves? What is their trade?
Ishmael watches the woman for about ten minutes to ensure she fits the description and also watches around moving about a bit while in the shadows to see if there seems to be anyone watching her or watching over her. He takes his time looking at particularly shadowy places where he would hide if he wanted to not be easily seen though was not as talented.
Eventually he moves away a bit, uses the hat to alter his appearance to something resembling a middle aged small time trader albeit with a tad expensive clothes though nothing too fancy. He also takes the necessary time and puts on a mundane disguise with the main effort being to cover his skulk characteristics, skin color etc in case they can somehow see through the magic. As always the hat is used to augment the basic disguise and there are not huge changes that will stand out like night and day if the magical disguise is pierced.
Satisfied he starts walking in the open, taking care to actually have his foot steps make a normal humans noise, and approaches where she stood.
"Hey there my dear lady" he says as he approaches.