Stories I've heard with no certainty of truth:
Some Lord used to have his valet wear his newly tailored suits to break them in before he wore them himself.
Fred Astaire used to throw his new suits against the wall a few times to soften them up.
Director Terrence Young took Connery to his tailor to be fitted for his Dr. No suits. Connery was a bit rough around the edges and not really in tune with the genteel lifestyle of Young (and Bond as written by Fleming), so learned a lot from Young, including sleeping in a new suit to break it in and feel comfortable in it when the cameras are rolling.
Love all of this!