First off: I have maybe 250,000 touring miles under my butt. I wonder about "Fun Shoes". Is that Flip Flops or Burkenstocks....? Just because you are on the back does not make you safe when you "Go Down". Both of you go down the same. BOOTS are in order...protect your ankles.
BTW: No matter how good you are...you will go down sooner or later. You will use up your allotment of miles. I no longer ride because I figure I'm close to my allotment. I'm 69.
Ride Safe First......and..... Then BE COOL.

NB