I mean it's dumb that they bought an outfit at Target for O and they never had him wear it, but I honestly don't see a big deal with J just wearing any red shirt he has to school. I get that the "rich" private school situation means the parents go overboard with the themes and outfits, but I guess I don't see the "poor J" aspect of this. I can't recall my kids owning a specific Valentine's Day shirt solely to wear to school. And yeah, they are at Target all the time and buying random tit so they could have gotten him a shirt... but, who cares? There are other things they deprive him of that are more pathetic or sad like candy in his stocking or having a whole cookie for V-day.
He was solely wearing the same shirt to half their staycations for a long time (the sun one), and it seems he doesn't like certain clothes/shoes. I bet he really dislikes longer or baggier shirts, as well.
And no, I am not sticking up for them. I just don't see the shirt as a big deal. They are guilty of way worse parenting "fails" than that. Some kids don't want new clothes or don't care either. If kids in his class make fun of him for that, so be it. Kids will get brutal as he gets older for more hurtful things like what his parents plastered all over YouTube.