>>18464573not OP but i cuff twice with the shirt off, setting both creases with an iron. a lot of shirt sleeves aren't symmetrical after some washes which makes them come undone, and the under-arm area hard to cuff evenly if you just do it while wearing it. i can't get single cuffs to stay this way (maybe if my arms were bigger) but double cuffs work. looser sleeves may come undone if you take a jacket off.
it also wasn't unheard of at all back then to sew the cuff on as well.