Oh yes Cindy, I've definitely got guilt issues lol - as DH would say "you Irish-Catholics *eyeroll*" ... or as I like to frame it, a high degree of conscientiousness!

Notsaf, you're bang on - and I think on the one hand, I want to try something a little fresher, while on the other, because I rarely need a dress pant, I am hesitant to spend on them. They are starting to wear a bit though, so I do think it's time! But it's not a high-pressure or time-sensitive need - so I can also chill and wait for the right pair at the right price (or to see where the new pants silhouettes settle over the next little while - it's still skinny-central in my town, although the cool girls at Aritzia and other trendy stores seem to be branching out).
Gigi, wise words and guidelines, thank you! xx

Shevia - this is why I adore you: "There is a lot of space between being wasteful and achieving the Platonic ideal of a wardrobe, which anyway assumes you are frozen in time." So smart and insightful. And that's so bang on - the Platonic ideal of some perfect pin-worthy closet image, which has little or nothing to do with the dynamism of being a human. Amen and I need to write this down somewhere that I'll see it often!

Lisa - I think that is a totally legitimate reason to turn things over though - one of the few, in a way! Things need to fit. And if you're passing frequently, then at least what you are passing it in great shape and probably an amazing find for smart thrifters!

I am very hard on footwear, and don’t expect them to last more than two years, especially bad weather boots and sneakers. The only shoes I own that are older are “party” shoes, which are seldom worn.

On the other hand, I have 5-6 sweaters that are 28-30 YEARS old, and were so well made that they have never pulled, retained their shape, not sagged etc. I think they will last another 20 years! Newer sweaters, not so much... I hope they will last 5-6 years, but it is definitely a crapshoot with quality these days.
Also own a 28 year old dress, several silk blouses, and some outerwear the same age. Classic styles, great quality I guess.

2-3 years generally. Since I have a smallish wardrobe, and essentially 2 long seasons- summer and winter with very little in between, things wear out. I feel I'm constantly replacing things, but it gives me an "excuse" for regular updates too!

The big lesson here is:

Analysis Paralysis is not a beautiful thing. Relax into your style. Don't let it boss you around. Life is full of hectic stresses. Let your wardrobe be the joy, and not the stress of your life.

Suntiger yet - and I think too with those long seasons, it's easy to get sick of things because I end up wearing them SO often (especially winter stuff for me) - so if I keep it smaller, wear things out, and then replace, that actually works really well.

Angie - analysis paralysis is my downfall, as you well know!! Wise words; thanks for them and for your steadfast and patient encouragement over the years! xx

Your winter is longer than mine, so maybe not a 50/50 split, but 60/40? Transitional wear just ends up being summer wear + topper, combo of summer and winter stuff, or winter without topper- so not much needed.

Unless you're in So Cal, and get to wear the transitional peep toe booties, short sleeve velvet, unlayerable kimonos, etc...

The feeling is mutual .