tell me about the swaggiest outfit you can imagine kimber wearing but he had to pick it out himself
so the thing about Kimber is that he is not dressing swagfully when he picks his own clothes. He wears a black t-shirt and olive green fatigues and the same belt he's had since he was a teenager every day. On missions he also wears a brown aviator jacket. This is an outfit that looks good on everyone so it's fine but it is unusual for his context.
Kimber grew up in the Human Survival Organization (HSO)—New Blue City's militarized humanist faction known for its values of ingenuity and creativity. Basically every other HSO pilot and most of Kimber's HSO peers are dressing hot and distinctive on purpose. (Parlance and Church of New Eden pilots derogatorily call HSO pilots "runway dogs").
Kimber's dearest friends Jamison Glass and Thrash Harrower have great senses of style! His current squadmates on Astrolabe are fashionable! Kimber's sister Lettie is a fashion designer. None of this has helped him. I guess some of the t-shirts he wears are navy or dark grey instead of black? This man is forty-two. He is not going to dress differently. Now that Astrolabe is famous at least it's easy to decide what outfit to put Kimber Kelsey in when the Parlance Corporation makes merch.
When he is attending a function where he has to dress up his sister Lettie or his squadmates pick his outfit. And back when he was ... involved with (?) General Mhonday Fang, he was not picking his own clothes for public functions, he was told / sent what to wear.
^ I had this answer mostly drafted before the session but Kimber did go on a date with Thrash last night in the opening scene of S3E7 and SO to actually answer your question: he wore a navy denim button down instead of a t-shirt because he knew it would be meaningful to Thrash if he dressed up (relative). And it was.
