Not sure if this has already been discussed on the forum, but I am a fan of the "Wrong Shoe Theory":

I have actually been doing similar for a while thinking of it more as "try the unexpected shoe". It came about from the trial and error of trying all potential shoes with an outfit and very often ending up happiest with the option I least expected. It may speak to a lack of imagination or styling skills on my part more than anything else! But it has become more intuitive now, such that I think of formerly weird-to-me pairings first. Case in point, for my heatwave outfit today I chose these blush Buckleys rather than the cream Birk Arizonas, or white, metallic and cognac sandals that I would have found "obvious" in the past.

Would love to hear and see others' thoughts!