Travel footwear has to serve the itinerary, not an imagined version of it. List the real surfaces, weather, walking time and dress requirements before choosing pairs. A compact travel wardrobe works when every shoe has a clear role and can support more than one outfit.
Build around the longest day
Select the pair that can handle the most demanding walking day first. Test it with the socks or hosiery you will pack and check space after several hours, when feet may swell. A second pair should change function, such as rain protection or a dressier evening, rather than duplicate the first in another colour.
Check trousers and hems together
Try every planned bottom with both pairs. Wide trousers, long skirts and dresses may require different sole heights, while cropped trousers expose more of the shoe. Adjust hems before travel rather than relying on an unsuitable shoe to rescue the length.
Pack for recovery
Allow shoes to dry and air between wears. Use lightweight shoe bags and fill the interior only with clean, soft items that will not deform the shape. If a pair needs breaking in, it is not ready for the trip. The goal is fewer shoes with proven comfort, not the smallest number at any cost.