Originally Posted by mdubs
Sir, you bring up many good points that I probably should have mentioned.
I live in Southern California, so I do not need warm or cool weather shoes, as the weather just doesn't fluctuate much here.
For rainy days, I have two sets of Bostonians that I wear (a set at home and a set at the office). For lighter raining days, or days with a decently low probability of rain, I wear my Alden Perforated Cap Toes in Color 8 or my Allen Edmonds Cambridges in Burgundy Shell. Those two are also my travel shoes. I picked them solely because of their age and the darker color can withstand more of a beating without showing flaws.
I am not unhappy with any of my shoes in particular and I do a decent job of rotating through my shoes. I am unhappy with how long I take to phase my shoes in though, but that is more a issue with me wanting to baby my new shoes. My main predicament is that I am honestly running low on places to store them... :-)
Yeah, I should have figured you lived in a warm weather climate given the relative lack of high boots. I definitely cycle through shoes seasonally. I wore my cigar LSH multiple times a week during the summer and have stopped wearing them. Right now I am wearing boots (wore Leffot tankers today, will wear Context tankers tomorrow, wore AoC wingtip boots and Alden black captoes last weekend, etc) so my casual bluchers aren't getting as much wear. I try to break them out on Fridays. Come summer, boots will be sparingly worn.
If you rotate your shoes, then clearly you get value out of all of them. There are some shoes (mainly ones that I bought because they were "special makeups" or "rare" or something like that) that I wore once or twice then sat ignored for weeks or months, largely because I prefered an other older pair (these include cigar PTBs, cigar Indy boots, Leffot antique color 8 naval boots, whiskey NSTs, etc). Those types of shoes I sell.