To me this song speaks to a an anxiety you might get about how you present yourself to a women. To me, the 'black shoes' speaks to a white collar upbringing and 'brown shoes' speaks to a more blue collar upbringing. The way class plays into romantic relationships is slightly alluded to when David Berman, pretty clearly references the Greek story of King Midas. On one hand you want to portray yourself as well off and free of disorder to a possible date, but this clearly isn't David's personal experience and life's been hard for him, so I think he's wondering 'should I portray myself as a normal, in control person or let this person in on who I really am with all my trials and tribulations?'
To me this song speaks to a an anxiety you might get about how you present yourself to a women. To me, the 'black shoes' speaks to a white collar upbringing and 'brown shoes' speaks to a more blue collar upbringing. The way class plays into romantic relationships is slightly alluded to when David Berman, pretty clearly references the Greek story of King Midas. On one hand you want to portray yourself as well off and free of disorder to a possible date, but this clearly isn't David's personal experience and life's been hard for him, so I think he's wondering 'should I portray myself as a normal, in control person or let this person in on who I really am with all my trials and tribulations?'