I’ve found that it helps to keep a list of what I currently have, along with noting particular styles that I’d like to add in the future. I also try to avoid owning multiple shoes/boots in similar styles & colors. In my opinion, having to spend time on routine care for leather shoes is enough incentive to avoid having a bigger collection.

For dress shoes, I’ve got 9, though one is a black cap toe that I only wear for formal occasions. Of the remaining 8, some get more wear in spring/summer and others get more wear in fall/winter.

When I’m not in dress shoes I’m usually in sneakers in summer and boots in fall/winter/spring. I think I’ve got 3 or 4 sneakers and 7 or 8 boots, all different colors or styles. Add in two pairs of non-dress shoes, gym shoes, duck boots and insulated winter boots and I’m right around 25.