How long should you keep/ wear leather shoes?

It depends on wear: As long as the soles are not worn down and uneven, leather shoes can usually last a long time. However, living in new orleans, i would advise you to make sure you air out the shoes regularly and disinfect them to prevent fungus and moisture to damage them.

Depends: It depends on how often you wear them, how worn the soles, heels and upper leather are. If being worn almost daily i would say a year.