Maybe I’ll be seen as boring for making this rule for myself, but my second rule for myself is to buy only comfortable shoes, the reason being that: I’d rather have happy feet that will last me many years to come rather than suffer in my later age with things like plantar fasciitis. I’d rather look imperfect in the shoes I wear today and be able to run and jump and be pain free tomorrow. Some shoes allow us to meet in the middle and manage to serve both form and function, so it isn’t to say that I can only buy unattractive shoes, all the shoes I buy can look nice as long as they’re also comfortable. I’m not going to force myself to go out and replace all my shoes all at once, but rather to keep this rule in mind each time I’m ready to buy new ones. So for shoes: function before aesthetic. So converse, my old friend, so long you attractive but poorly supported shoe and no more hard soles or overly high heels for me either (at least none of the high heels with the steep angles that arch my foot too much).