I've asked this to others before so forgive me but for the kink asks: to what degree does Toby really have a Thing for the Catholic school girl uniform? And does Andy share it?
oh no worries! the more thoughts, the merrier!
toby & andy & the schoolgirl uniform:
toby having gone to public school never had uniforms but growing up, he saw the rich kids wearing nice, expensive, matching dress shirts and skirts on the street and on the train. he thinks the girls are cute, the guys look good. he feels like it's a little weird, a little too homogenous. where's the individuality? he couldn't afford those, anyway, not the school and the clothes. but he went to Hebrew school on sundays with his siblings (which i don't believe has uniforms but you do need to dress appropriately).
and hold on to this thought -> there was a 1964 US appeals court case in brooklyn where a federal judge actually ruled for allotting time for voluntary prayer in public school. so exactly around when toby sits out the prayer in grade school and gets beat up for it, there's this legal case that says he's in the wrong. he is standing firm in his beliefs, he is withdrawing himself from something that is not his, and he gets beat up for it.
say andy went to a religious all-girls high school, and toby saw her school photos when he visited her parents' house. he thinks she looked cute at sixteen, braces, the little jacket and tartan bowtie.
now the actual uniform and trying to emulate it... after a phase of pretty vanilla sex (nothing wrong with that, but there's something missing), toby makes a proposal to shake up their sex life with a bit of roleplay. because it's a cliche that eveeerryyyyyy guy has a fantasy of being with a pretty young thing in her school uniform. he doesn't say it like That, but close enough. he thinks it would be sexy to see andy wearing a plaid skirt and knee socks and Mary Janes.
andy thinks toby's idea is ridiculous. she hated that uniform! it was itchy and hot and she wanted to wear her favorite blouse. not the button up. but she's like "what the hell", just this once. she digs around in her closet for something similar enough. when the mood is right, they go through the scene. she straightens her hair and wears a headband for maximum effect, and she still feels ridiculous, playing up the flirting and teasing and it's funny seeing him flustered because of her! lots of bad puns ("we must have chemistry together", "i've been bad," etc.). then toby says something, and andy remembers having a crush on her teacher when she was seventeen. he was a very cute teacher. married, too.
the skirt's nice, the sex was a little more energetic this time, it did something for him but not much for her.
it doesn't really mean anything other than toby has unresolved trauma around voluntary prayer in public school and those expensive uniforms he never wore. so of course a Jewish man wants to see what it's like to be with a Catholic schoolgirl.