I feel like Jeremy dresses in a way where he tries to be cool but is also not confident enough to really commit. Like he’ll wear whatever is “cool” at the time, but he lacks the self worth to believe he can pull it off. So he kind of half-asses it and keep wearing the cardigan and kind of goofy tshirts because they’re safe. And what? The cardigan is comfortable and he likes it. He’s in this weird limbo of wearing some stuff “right,” wearing other stuff “wrong” and all the while horrifically uncomfortable in his own skin regardless of what he tries.
So when the squip changes his whole fit into something “cooler” Jeremy finally gets to feel like he’s wearing something coordinated and fashionable. Like he’s allowed to feel good about it because the squip tells him what the “right thing” to wear is. He doesn’t have to be worried about whether he’s doing fashion wrong. He doesn’t have to worry if people think he’s trying too hard and failing, because this Keanu reeves lookalike knows everything already and is telling him what to do so it’s ok.