The thing that I find most adorable and compelling about Box/CRT Vox is the fact that immediately before his death, he was desperate, grand and over-the-top glamorous. Something about dying led him to go back to a more muted, sweatervest kind of "earnest" look.
It's entirely speculation, but I headcanon the anonymous nature of Hell lets him almost revert to his softer self, the version of his mask closer to who he is, vs an extreme copy of other people. He's still a serial killer, by no means is he harmless, but he's more honest at this point.
I think this anonymous edge is why he even dares to reach out romantically to another man in the first place, it allows him to try and define a new version of himself, a persona built from the ground up. It's an act of confidence from an insecure man. Alastor's rejection knocks it.
After this, we aren't sure what happens to Vox, but we do know that he sticks to sweaters, he tries to cling to that sense of self-expression he started out with. He doesn't fall back to the suits he wore on television I'm going to subject you to his sweatervests as a symbol of his "true self"
He keeps this style right through the 90s (I assume 90s because of the composite RCA ports in his head) which to me implies his rise and relationship with Val allowed him to retain a bit of himself. Val supports him, but also shapes him in his own way.
I think Valentino loves Vox but there is part of him that wants a sexy CEO partner that fits a certain fantasy, he roasts people who are fat for e.g and Vox becomes concerned about his/Shok.wav's weight ("you know those are bad for you", about sodas) He alters himself physically and sexually.
That doesn't mean this is a 100 percent toxic thing either, people DO change naturally in relationships, I think there's an abusive edge to image control here, but I think there is a softer part of this change where Vox tries to become the amazing, impressive self Val sees in his paintings too.
To me there's a tragedy to Vox's eventual slick, trim CEO version he settles on once Alastor goes missing. He dons his style, mirroring his outfit in his own attire in an act of what to me feels like a mixture of devotion, tribute and complete surrender of his own inherent sense of self.
And yet he still has a sweatervest underneath. We see it when the exorcism is happening and he has his coat off and sleeves rolled up (incidentally -fans self-) He's never dropped it, just hid it.
With Lucifer, he mimics his outfit, trying to subvert his power in Hell and directly challenging his role as a self-appointed "King". However again, to me it's showing Vox's insecurity, he mimics the person he wants to overtake. And he's still uncertain about it, asking how he looks.
In the finale we see Vox in an outfit he almost certainly chose for himself, breaking away from the (gorgeous) matching outfits that Vel designed for the team and wearing his own techbro trenchcoat He's asserting his new idea of himself and his individuality, but at the wrong moment.
But when everything falls apart and all of his walls fall down, exposing his truest, barest, rawest nature in the final moments of the series, the arms of his outfit are tattered.
He just can't escape who he really is.
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