For the majority of her life, Jolie has had the luxury of speaking her mind when she wants to. Her family isn't as old money as the Reagans and she doesn't have the political connections of a Blackwood, but she's been cultured to believe that she doesn't have to exercise much tact for anyone on or below her level. Given the way he was yelling earlier, it may not have been the best idea to make an offer like that, but she's not the type to pull him aside later and tell him he looks stupid.

Either way, in her eyes, she's coming off successful. If he turns her down, he continues to look like shit by her standards and if he says yes then she's presented with yet another opportunity to do her part as a Stylist and do something nice for a guy who could probably use a hug and a psych more than a suit.

A sly smile returns to her lips when the small moment of dread for an unpleasant reaction passes. "It'll be like the Emperor's new clothes all over again, then." She chuckles, keeping her smile in check when he acts agreeable. "It'd be my pleasure. You know I like it when I can get pretty people in my clothes." She pulls a face, dramatized for emphasis. "Pick up line not intended, of course."