do you think Lily and Remus just sometimes bonded over how good boys in skirts look?
Remus first noticed this when he slept in one day in third year and stumbled down into the common room only to find James taking pictures of Sirius twirling in a checkered skirt
he stopped dead and just stood at the bottom of the boys‘ dormitories stairs staring in disbelief at Sirius‘ long pretty legs
it was only when Peter bumped into him, still oblivious as to what was going on in Remus‘ mind because he, too, had just woken up, that Remus got to his senses
luckily, none of the others had noticed him and he was spared the awkwardness, but he politely refused to dance with Sirius for the photos when asked. he didn’t trust himself.
when he befriended Lily around fourth or fifth year, Sirius walking around in skirts had become a fairly regular occurrence (as an expression of himself as well as a simple fuck you to his family)
but while Remus liked to pretend it didn’t affect him all that much anymore, he latched onto the topic pretty quickly when Lily mentioned how she really liked skirts on boys
Lily hadn’t even said Sirius‘ name (though she did have him in mind; the whole school agreed that he was a very handsome boy, if sometimes a bit arrogant seeming), but Remus didn’t stop talking about his legs and how pretty they looked when he twirled in his skirt and how he wished more boys would wear that for about twenty minutes
Lily just smiled knowingly and nodded along and knew she‘d found a new best friend because he was just so endearing plus one of the few people at that time who openly and definitely agreed with her on that topic
she‘d always been very straight forward about not caring for any gender norms, and her friends being on the same page as her was very important to her
it was also one of the reasons she slowly started to appreciate James more; once, Remus told her the story of Sirius‘ first time wearing a skirt and she couldn’t stop thinking of the way James was incredibly supportive of his friend embracing himself for a day or so
she would absolutely deny that fact to anybody who slightly assumed anything like it though
at one point in sixth year, when Remus and Sirius finally got together and Lily and James had become tentative friends, Remus persuaded James to try on one of Sirius‘ skirts to woo Lily
she tried her best not to obviously stare (she failed) but that night she couldn’t stop telling Remus about it.
at some point it had become some sort of ritual for the two of them to sit in the common room late at night just talking about how great men in skirts look (some very particular men reoccurred quite often)
they continued doing this on a regular basis after school. sometimes Sirius would join in and try to persuade Remus to try on a skirt, but he‘d always refuse
when James and Lily died, and Sirius went to Azkaban, Remus couldn’t bear seeing men wearing skirts for a few months
after that, he tentatively started to sometimes put on a skirt, just staring sadly at his mirror, wishing Lily were here to reassure him, and imagining he wasn’t looking at his own reflection but at Sirius instead
he had one of Sirius‘ old skirts which was his comfort skirt, it had been Lily’s favorite and when Sirius had found out, he‘d started to wear it more often.
whenever Remus missed one of them especially much he‘d lie on his bed clutching said skirt, sobbing into it, and he didn’t give it away even when it almost looked like a rag