Just wanted to say I use the “iconic” category to give myself permission to buy and keep a small number of items that won’t get worn a lot. Now that I work from home my lifestyle is quite casual, but dressier, “going out” items give me MUCH MORE joy than casual, everyday items. This is my way of finding a balance.
I deliberately use the word “iconic” to set the benchmark high. It really makes me analyse whether an item that is only going to get occasional wear is worthy of a place in my wardrobe. And my definition of iconic is personal to me, like Sally said. There should be signature elements. Aspects that I have consistently gravitated to over time. Maybe a HEWI element. Not too “of the moment”. Also ageless. Would this be age appropriate (for me) in 10 years time? And good quality. Likely to last.
But, to reiterate, iconic doesn’t have to be expensive or statement-ish. I class these pants as iconic (for me). They are great quality, interesting, classic, not expensive. Iconic for me because I love full length, tailored, wide leg pants and have never really been on board with cropped or slim leg pants (which might be iconic for someone else). They don’t get a lot of wear because I favour jeans, skirts and shorts for everyday wear. But I do occasionally enjoy wearing dressier pants. I’ve had these for 3, maybe 4, years now and have not tired of them in any way. Size and wear permitting, I imagine I will have them for some years yet. They give me joy.
So, ST, getting back to your original problem. I think 10 “iconic” items a year would be too much if you only have a small wardrobe and you plan to keep them for a long time. Maybe one iconic item per season? Also, it depends on if you find them. Some seasons you might find 2 or 3, some none at all.