Pack shoes for a city break around the longest walk
Start with your longest walking day. Think about its surfaces, any stairs and whether you can return to your room before dinner. The shoe you can wear for that whole route deserves the main place in your packing plan.
Make the walking pair your baseline
Use shoes you have already walked in on a similar day. Pair them with trousers or a skirt that clears the ground at that shoe height. If the weather may change, check the sole and upper for the surfaces you expect. A second pair is useful if it fills a real gap, such as a dress code or a wet route, and if you will have a place to change. Two pairs that do the same job may take up space without helping.
Pack clothes that work with both pairs
Lay out one daytime outfit and one evening outfit, then try each with the walking pair. A knit and jeans is a simple starting point when it suits the weather. Check hems and colors with the optional second pair. If only one outfit needs that shoe and the event is flexible, adjust the outfit instead of packing around it.
Check the return route
A late walk from a restaurant can still involve cobbles, hills or a long station platform. If the second pair is only comfortable for short distances, plan where you will change or choose a different pair. Keep room in your bag for the layer you will remove indoors.