Bob Dylan: Positively 4th Street [purchase]
No survey of footwear in song could be complete without a nod to the greatest lines ever written featuring shoes. Now, this song doesn't actually include footwear in the title nor highlights footwear in any other respect, so I've excerpted the brief, shoe-centric bit of genius.
On a totally self-indulgent note, when I was a senior in high school I was a delivery guy for Lino's Pizzeria in Huntington Beach, and my co-worker, Steve, quoted this exact verse as an example of Dylan's brilliance. So, upon his hearty recommendation, I went to Licorice Pizza the next day, bought the Greatest Hits, and was summarily hooked on the Bobster. So, here it is ... the verse that turned me into a Dylan fan and showed every songwriter how to properly say, "Fuck You!"