"I would manage," comes the response, not defensive or tinged with anything besides flat factual delivery. Illumi elects to interpret 'homeless' as somehow neatly tying up the loose ends that would be what becomes of his family, in this situation, so yes - objectively speaking, he could manage the vagabond life. Creature comforts do nothing for him, anyway.

Those shoes are absolutely criminal. Hisoka's obsession with heels mystifies Illumi; is he not tall enough...? Truly, he'd be a horrible assassin. Illumi folds his arms and leans against the shelf with not so much as a second glance at the shoes, despite- how bizarre they are.

"You are memorable." Again, factual. "I know your style." He pauses, like this is a simple conflict of stealthy fashion and not Hisoka being too flashy for his own austere life. Then- "In that case, pick something you don't like."