My mother dressed us all as very eclectically and I imagine that as the only boy in the family, little Rupert would have had extra attention paid to his wardrobe. I see Mum dressing Rupert in a Croatian patchwork poncho over a Batman t shirt and raspberry coloured woolen cardigan, tucked into olive coloured corduroy pants held up by patterned suspenders with shiny little red gumboots. I envisage tiny John Lennon glasses, too.
Rupert probably would have been a bit reserved and shy, as you would be after being teased so mercilessly about your clothes at school. I think would have grown up to be adorable to the girls he tutored English Lit 101, especially when he took off his glasses to clean them during class and had to squint a little.