Starting to become comfortable
Remus came into the ROR a couple weeks after Severus was wearing the dress to see him wearing more clothes like that.
His hair was pulled back into a high ponytail with rainbow cat ears. He was wearing basic makeup and blue nail polish. Besides that he had on a slightly oversize purple sweater and some blue jean shorts. Lastly he wasn't wearing shoes, however he did have on rainbow ankle socks.
Remus walked over to sit across from him.
Once Severus noticed he was there he stiffed but didn't say anything.
"Hey, cutie." Remus began the conversation.
"Hi, Rem." the other boy said quietly.
Pausing for a second Severus continued "Do you, do you like what I'm wearing?"
"Of course, love. I like everything you wear. Though what's really important is how you feel about your clothes. So, do you like them?"
"Yeah. Yeah, I really do."
"I'm glad."
Remus pulled out a book and the two began quietly reading together.