Gah, this is such a great topic! You've gotten so much great advice already. I'm nodding along with those who have pointed out that many of these items present seasonal/weather-related challenges, and come the (ever so fleeting) spring, you might feel differently. I'm always looking at items that won't really work in deep winter or high summer, and asking myself if it's worth having an item I'll only bring out a few weeks each year.
It also strikes me that several of these items fall into your "event" capsule -- and I know you're a strong proponent of not sweating too much over cost-per-wear on special event clothing. But maybe even if wear-tracking in a traditional sense doesn't work for a dressy capsule, perhaps there needs to be some system for joy-tracking? It sounds like the Vince dress has served its purpose and doesn't make you happy when you wear it anymore. It actually stands out, among this group of items, as a piece from an earlier style era of yours. It feels out of sync with your more recent additions. The newer "event" items (the gilet, the sequined culottes) -- I would keep them and play with them. Perhaps try wearing them dressed down for casual days, even, just to break their spell. Agree that perhaps the gilet needs its own coat if you want to wear it properly, because that seems like a prime winter topper to me. I don't have any, but if I find the right wool vest or gilet, I will add it in a heartbeat, as it could solve some of my dislike for toppers/third pieces this time of year. Of course, this could just be a case of theory vs practice on my part. This winter layering business -- who knew it was so complicated?
I can commiserate with you on red pants. I've just had to accept that I'm happier not drawing attention to my legs. I've found that prints are totally okay (Im up to four, FOUR! pairs of patterned pants), as long as they are dark, neutral, and fairly low contrast. And a great fit, of course. But *bright* pants? Ugh. The last time I had red pants, they felt by turns like PJs or a Santa Claus costume. It was completely psychological, because they were sturdy woven pants with pockets and a fly, but I just couldn't get over how weird I felt in them. Red Pants Syndrome, I guess.
And the boots -- I feel you on this one, because I do the exact opposite. I look at all the pretty boots, then patiently talk myself out of buying them, because the winter will destroy them -- and when the weather is nice enough, will I really want to wear boots? Probably not. And then when a winter event rolls around I have nothing to wear. I know you have a good collection of more refined boots that *are* weather-worthy, so it's hard to judge how much utility these more delicate options will have for you. I'd say there's nothing wrong with having some indoor-only options, as long as you feel the styles have some longevity so you can bring them out once or twice a year for several more years to come.
I do like the idea of chopping the sleeves on the bell sleeve top. The bell sleeves were an experiment, they failed, why not turn the top into a new experiment on the effectiveness of modifying sleeves? Or... make a point of wearing the bell sleeves with the gilet once or twice this spring, when it's warm enough for the gilet to be your outer layer. And if you like the combo, maybe you give both pieces a new lease on life.
I do hope you find some good silver buttons for the pink blazer -- I was so, so tempted by that piece last year, but the gold was off-putting, and I have enough chores without adding "change out buttons on brand new jacket" to the list. So I'd like to live vicariously through you on that one, please.