So, step into (pun intended) the world of the most expensive shoes ever sold, including insights into their sky-high price tags. 1. Michael Jordan’s ‘Dynasty Collection’ Air Jordans.

What you'll pay: The classic Derby lace-ups from Rollie have a $190 list price in both conventional men's and women's sizes. Boots go up to $220, and you can get sandals and slides for $140.

The derby was often worn as a more practical countryside shoe, which accounts for the greater variety in styles available—there are sophisticated, slim-soled derbies that would look right at ...

From festive flats to heels that will keep you feeling comfortable all day, these are the best women's shoes to wear tot he Kentucky Derby. 1. Margaux The City Sandal. $345 at Margauxny .