Here are some cute children's dress shoes (yes, probably the kind that hurt your feet) from the 50s .
I think Buster Brown may have shoed the majority of dressed up children's feet. Price range 1958 $5.99-$7.99
March 3, 1958 Life Magazine
Sundial Shoes for Children Price Range $3.95-$7.95 in 1955
March 28, 1955 Life Magazine
Buster Brown's price range $5.99-$7.99 in 1958
January 6, 1958 Life Magazine
I'm not getting the history link at the Brown Shoe Company to work for 1943- 1987 to find out more about Robin Hood shoes - price ranges $4.99-$6.99. According to this link
The Brown Shoe Company, manufacturers of shoes, also published comics during the 40’s and 50’s, these were not sold along with other comics but could only be found in shops that sold Buster Brown and Robin Hood brand shoes.
March 17, 1958 Life Magazine
Buster Brown's price range $5.99-$7.99
March 24, 1958 Life Magazine
March 9, 1959 Life Magazine
Robin Hood's price range $4.99-$7.99
March 9, 1959 Life Magazine
And cute new Easter outfits from Sears price range $6.00-$6.98.
March 16, 1962 Life Magazine
Even though I know dressing up formally is the bane of existence for many children, these fresh outfits and shoes make me smile.