I’ve noticed the same thing while walking on older stone streets and uneven industrial flooring. Trail-running shoes usually work better because the outsole compound and tread pattern are designed for grip and shock absorption on irregular surfaces. Softer EVA midsoles alone are not always enough if the sole lacks stability.
A lot of performance footwear today also uses specialized rubber compounds to improve traction, durability, and vibration control on rough surfaces. Material selection in the sole really makes a difference for long walking comfort and reducing foot fatigue.
Interesting discussion overall — especially how different sole materials behave on cobblestones versus smooth pavement. By the way, I work with industrial rubber material solutions at I R Tubes Pvt Ltd, so I always find the material-engineering side of footwear pretty fascinating too.