Put a little more clothes on the youth and take away the bulge in his crotch, and this could pass for an American Normal Rockwell painting.  There is humor, and it begs for interpretation.  Is the seated dandy looking with envy at the comely young man while waiting his turn? Or is he a "sugar daddy" and paying for the new clothes for his sex toy?  Is the lad smiling at thoughts of his new clothes, or smiling because the tailor has firmly pressed his crotch and held it a little longer than the measuring required?  The one here whose wheel of fortune is going up is obviously the young man.