Considering how most pilots’ uniforms are maintained and fitted (including our dapper Spirit colleagues) and the culture they hire for, he’d probably get the job.

But in all seriousness OP, best bet is probably buy a cheap garment bag and carry it around for the trip even if you have to check your rollaboard for a commute/DH, do your best to keep it from getting crumpled. Shower steam it if you have to and you’ll be fine. Best part is if you take decent care of your work shoes, you won’t need to pack another pair unless you’re part of the Velcro or black new balance gang.