aries~ years ago, my nephew also dressed similarly to your youngest son… but he took it a step further: as a full-blown milkmaid (with blonde wig in braids)! my sister-in-law is veryy (Chassdishe) frum, & I’m surprised she allowed this cross-dressing, but I reallyy thought he was a girl!
my favorite, funny: me walking an invisible dog– on a stiff leash, with a stiff harness– down a couple of blocks & then down Avenue J, to shul. EVERYONE, especially me!, got such a kick out of it!! :))