I disagree with the take that Caitlyn actively dislikes feminine clothing for many reasons, but the main one is the fact that people say she was 'forced to wear a skirt because it's her uniform' when there's no proof for that. Yes, the skirt we see her wearing is part of the enforcer uniform, that's a fact, but there is no proof for the idea that Caitlyn was forced to wear it. There is, however, content that suggests Caitlyn isn't bothered by the skirt.
(I'm not trying to hate on people who think that Caitlyn is more masc, it's completely okay to have headcanons !! It just bothers me when people act like it's canon despite there being no actual evidence, and this is just my interpretation c: )
A female Enforcer, just like Caitlyn, but she wore trousers with her uniform. Now yes, I hear you, I will concede to the point that Grayson was the sheriff and so maybe the sheriff uniform is just different to the normal officer one... which is why I now propose:
This time a normal Enforcer, not a special rank or anything. Just an ordinary, female enforcer, wearing trousers.
Not an Enforcer officially but she did put on one of their uniforms to fight, and, once again, what she put on has trousers. What she put on does seem to be a different style of uniform entirely with more armour, but I think that just further enforces the idea that there are many variants of the Enforcer uniform and it's not a rigid system like 'boys must wear this and girls must wear that'.
Exhibit D: The unnamed Enforcer who tells Jinx she looks like a half-eaten circus tent
Listening to them talk, their voice sounds feminine. And what are they wearing? Trousers.
Jinx steals the unnamed Enforcer's uniform to sneak in, trousers and all, and she's then flirted with by a male Enforcer on the opposite side of the train, implying he was aware that she was a girl and therefore that it's normal for female Enforcers to wear trousers with their uniforms.
Caitlyn was not forced to wear the uniform with a skirt. And even if she didn't choose, there is still no evidence that she actively dislikes feminine clothing. She continues wearing the uniform even after she's fired to go break Vi out of prison - she didn't have to do that. Jayce was on the council by this point and she used his signature to get Vi out in the first place, she could've easily chose to wear something else and used Jayce's name/the job offer he gave her to allow herself access into Stillwater if she really hated the skirt so much. But she didn't, so clearly she didn't hate it. She also wears the uniform dress, just without the armour, when she's opening letters after Cassandra's murder. She wasn't on duty - she was at home, in her own house - no one was forcing her to do that. The robe set she wears when sleeping with Maddie is feminine and was her choice; the purple top she wears when Jayce visits her has a cutesy little bow on the back, is very low-cut, and is long enough to be a mini nightdress without the shorts underneath. She was wearing a skort (look closely, there are two layers of clothing on her legs, the skirt part even has a cute little slit) during the rain scene when she's 16. Caitlyn canonically dabbles in femininity of her own free will when she feels like it.
I also refute the idea when people use her Zaun disguise outfit as evidence that she prefers more masculine clothing because she didn't choose that either! Vi chose it for her, from beating up those two Zaunites, and she beat them up specifically simply because they were there and available!
For the record, I don't disagree with the idea that Caitlyn is a prince - she absolutely is a prince. She's a femme, yes, but she's a handsome femme. However she isn't as black and white as people making this claim think; she can do both, and she does do both. She's versatile and androgynous. Would she wear that suit? Yes. Would she wear that dress? Yes. She would wear both and she would look beautiful either way because she's Caitlyn fucking Kiramman.
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