You can read the fact Roman Roy spent most of the Succession finale wearing a T-shirt made for little children, currently for sale in a two-pack at Walmart for $13.96, a few different ways.
First, when he washed up at his mother’s house in Barbados, there was nothing else to wear. Perhaps he fled there straight from being trampled in New York’s post-election riot (the one he more or less single-handedly caused, lest we forget) without having time to pack any of his snug Gucci button-downs, and the one he had on already was soaked with blood, and so he had to wear whatever Caroline had lying around. This is the theory for people who believe “it’s not that deep.”
But of course, on Succession, the clothes are that deep—deliberate and clever, and very much in on whatever invariably sad joke the script is telling: Kendall’s pathetic spaceman jacket as he tried to launch his latest fight back for Waystar Royco. Tom’s try-hard white trainers in the Nordic mountains. In the pilot, when Cousin Greg is forced to flail around in an amusement park mascot outfit, that wasn’t just a piece of slapstick comedy—it was a statement of intent from a costume department with Things To Say, and the show has been richer for it. In this reading, the Walmart T-shirt is simply part of the “Great Infantilization of Roman Roy.” After Logan died, Roman tried to imitate his father’s heartless-bastard routine, firing Gerri (mistake number one) and prematurely calling the election for the demagogic Mencken (mistake number two). But at Logan’s funeral, Roman broke down in tears and ended up running back to mother, where his big bro and sister had to show up and convince him to come back out and play. Roman has regressed to being the baby of the family again, and his T-shirt proves it. Case closed.