A serious question.
Hmm) Let's be reasonable, i.e., consistent. Let's consider all cases:
1. Weekday.
To work by eight, alarm at 7.10 (how can you not steal 10 minutes of morning sleep, just in case you have a dream). Cash gets up at 7.50, because he dreams, and he dreams. At work by 8.05. In these 15 minutes, no one can keep track of the sequence of his dressing, not even him, because he also needs to have time to shave (or brush his teeth - your choice) and boil-drink tea (or pour milk for Masa - your choice). He puts on first what is closer.
2. Weekend.
Easy life. We slap barefoot in our underwear to the kitchen to put on the morning (rather, lunchtime) kettle, and halfway there, we turn on the computer. Masa tries all the time to grab his bare heel and flies off to the corner as usual. He puts on first what will get cold sooner.
3. Woke up at home not alone...
Well, it depends on whether he undressed at night - if not, then you don't need to dress. If yes, then he probably undressed consciously, and maybe he shouldn't dress yet...
Well, that's it. :)