Sure, but I'd imagine the average human could walk substantially further on flat modern roads in modern footwear than on cobblestone with ancient sandles.
You use 10–20% more energy for just mildly uneven surfaces - probably more for roman cobblestone.
Actually no. Uniform flat surface is tiring compared to a trail even in best shoes. Try walking 10 km on hardtop then compare to walking same distance on unpaved road.
For shoes we also went not too far: Merrel sandals basically replicate roman caliga with modern materials. And it's not like you can use even halfboots in mediterannean unless it's winter - it's just too hot.