I seem to find transitional season dressing very hard and vow each yeat to do better.
The weather will warm a bit and I will wear things that are lighter and then freeze in office, or conversely wear a winter sweater and it later seems too warm. I know about layering, of course, but usually don't wear a true warm topper at work.

Things that help are in the fabrication--for example, silky blouses are just not warm but may be too hot (sticky) later, go figure! So things I call "lofty" thicker cotton knits, or thin merino knits, work better. Also, I may actually find the right underlayers are as good for transition as for deep cold--maybe silk and cotton help even out temp changes. I may try going more transeasional with my thinner linen knitwear by adding a better underlayer. It makes me think that thin woven blouses, which I like for adding a feminine touch to some classic items, are just difficult.

Also, though I have tended to do a big seasonal rotation in spring and fall, I also find myself looking at items earlier and if I'm being honest, I will be saying, "I don't think I'm really going to wear you any more this season". It is part of admitting that I have other items "coming due" , perhaps cold-spring colors, or fabric weight, and it will split wears too much to keep wearing some of my other items.
That process is kind of weird because it may lead to thinking, hm, if I'm not going to wear it any more until almost next year , will I still like it or DO I like it? I might feel remorse that I did not wear it as much as I thought I would, so have to ask, is it not versatile enough, or too outfit-specific, or type of work day, or what?
Or it might prompt trying to see, am I "retiring" it for really good reason--perhaps it goes best with a particular deep-winter outfit for which the weather has now passed, or maybe I want to put a few woolen items in good anti-moth storage and not have so many out and "at risk" at once.

I'm also trying to look at this not only as out-of-sight storage (needed for wool) but for location-rotation within the main closet. Like moving an early spring capsule front and center and retired items downstream but still in the closet and not a true seasonal swap-out completely.

How about you--do you not only make seasonal swaps/capsules but also make item-by-item decisions to "retire" something until its season comes around again? Do you worry that its retirement may also be the kiss of death?