Same here - Comfortably "broke-in" jeans and T-shirts and sneakers that range from "gonna use one last time on a dirty job" to "less than a year old dressy occasions".
Not sure using change for purchases will protect anyone - those that will rob/kill you for ten bucks will do the same for ten cents if it increases what they have. Being well armed and situationally aware while limiting exposure is probably the best bet. Having a partner so you can watch each other's backs would also be handy.
The change tactic doesn’t work because you won’t carry enough. $48 in quarters for gas? Not.