Kirk gets it and bones cures it.
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The other way can be true, too. That Kirk wears it the proper way and Pike adds the undershirt for some reason. Or that regulations changed between the moment depicted with Pike and the moment depicted with Kirk.
It's not like Kirk is big on regulations on the first place...
No show-heading Captain really is though.
Pike is just the guy who wears an undershirt while Kirk barebacks his polos and buttondowns
you are supposed to wear an undershirt with a polo? that's just a collared tee
You don’t wear an undershirt with your tees?
i mean no i'm not [i'm not going to make fun of the religion here that would be rude, but i know a type]
You only have to if you’re at the YMCA
Kirk’s way is probably regulation. Here is a pic of mirror Archer wearing the green tunic without an undershirt. He looted it from the Defiant.


Kirk can get it
I'm willing to bet the undershirt is optional; Kirk was pretty good about following the rules most of the time. If he wasn't you know he'd have been tits out on duty, 100%.
He arguably was, given how many times his shirt got taken off or ruined.

My head canon is that when the Federation gets a new member the new folks get to pick the new uniforms. Troi's Betazeds came up with the miniskirts.
I like this canon, but I also like knowing that when Jellico ordered her into regulation uniforms like a big old meanie, it was actually because Marina Sirtis wanted to stop showing cleavage and be taken more seriously in her role.
I heard that story; that the cast used Jellico to stop all the things they disliked.
It's also interesting that different actors have a different response to situations.
It's amazing how often the cast on The Americans found the need to get naked in order to advance the plot.
look, some people can pull off a V and some people can't. it's not whoring, it's * ・゚:fashion:・゚ *:・゚
You imply that pike couldn't. I take offense in that
Could be both tbh. RCN NCD shirts could be worn with or without black T-shirt underneath. Most of us did choose to wear the T-shirt though as our NCDs were often so worn they were more titillatingly see-through than anything from Victoria's Secret.