This is such an interesting thread, Suz! Not least because I had an 'analysis attack' yesterday where I sat down and decided that I need to budget for about six new garments in certain categories for every year... and that I need them to be able to swap out last year's six. So I need six new shirts, six new tunics, six new pairs of shoes each year.
This came from realizing the same thing you did---I am more than happy to repeat the same outfit on a weekly basis, when it becomes a favourite for reasons of comfort, colour, silhouette (usually all three). And I am reminded that this is an old pattern for me---my mother used to get SO exasperated at my teenaged self because I was always picking the same things out of the laundry basket to wear twice or thrice a week... completely overlooking the last season's equivalent in perfectly fine fetter still!
Like you, I still held on to last season's favourites because they made me feel wasteful otherwise---how can I throw out something not only serviceable, but something that actually isn't necessarily outmoded, and spend some more replacing it when the budget is tight to start with? And so I ended up with an elephantine wardrobe of clothes I no longer wanted to wear or knew how to freshen up.
Indeed, my decision to have a smaller wardrobe in recent years comes from this precise place---if it's smaller to start with, a turnover won't be that expensive or irresponsible (I hope!).
I notice the four garments you show as examples are all pretty distinctive. In that they aren't 'background' or completer pieces. Does there very *presence* militate against longevity, do you suppose? To my mind, it is sort of a meat and potatoes thing (or perhaps, in context, rice and curry)---I don't expect the potatoes or the rice to change form; but I'd be pretty cranky even if you served me my favourite steak or curry for seasons together, even though they are 'favourites' and I'm happy to repeat them frequently through a fortnight. For me, I show favouritism for---as well as finally tire of---pieces that are decidedly NOT neutral (not in terms of colour; in terms of character or distinctiveness). Which means those are what Gaylene calls 'consumables' in my wardrobe.
In fact, the usual holes in my wardrobe are the bland neutrals that should be staples and links and completers. I barely 'notice' them when planning or shopping---which is why I'm often missing them... But I've realized THOSE are pieces that need to be 'investments' for me. I either need them in duplicates (or triplicates even), or need them in a more long-lasting quality; but above all, I need them to be NEUTRAL. Does that resonate at all? Maybe the items you love most and tire of soonest are the ones with maximum visibility, that read as one 'project', like Beth Ann said?
One thing to accept about the investments too, I think, is that they can be on 'repeated refresh' at a lower price point as well as a solid one-time purchase. What works will depend on the individual's lifestyle and environment too, as well as budgetary or style considerations. I can use the same pair of jeans for five years and keep at those 'neutrals' till they are hole-y because I don't wear them every day and don't crave variety in the silhouette or wash of them. My SO buys five at a time, all different, because he wears them every day and replaces them every couple of years but doesn't like to wear an 'uniform' (variety). Mine see laundry more often; his see more work and wear. Both represent investments; both sets are worn threadbare (workhorses); mine are usually mid-range while his are a mix of mid-range and budget because he replaces more and often. Our approach is exactly reversed when it comes to shoes... Maybe jackets are like that for you? Perhaps they need to be both workhorses as well as investments, so you need a mix of price points there to satisfy both variety and budget? And maybe, conversely, you need just a few skirts a season to favourite and then forget about?
Sorry about the long ramble. Guess I'm grappling with a wardrobe issue of my own and waiting for that elusive epiphany too... :-/