So cute!!! My parents did!!
I am ashamed to admit, I would "guide" him when picking outfits to go out in public. I normally encourage him to be independant and true to himself, but my issues with people's perception have gotten overpowered in htis issue. At home, he is always in his underwear, but I would let him wear whatever. I just wish he made it look so cute like Flora does, all he would do would be pick mismatching colors.
I too was overly concerned about people's perceptions, so I did all of the picking out of outfits when my darling girl was young. I was a newly single mom; looking back I'm sure I thought that if my kid looked matched and tidy, then it would indicate that I "had it together".