I'll throw in a few points here I guess.
While philosophically I agree with the idea of finding the 'best version of something', I also hate to 'make a mistake' but committing to an item which I'm not sure is going to work for me, or I'm not sure if I've found exactly quite the right version of, especially when I have limited resources, whether they be money, space, etc. So one of my techniques has been to use fast fashion, ie Gap/H&M etc to buy a simple basic version of something that's an experiment for me, and if I find I'm constantly using and enjoying the item, then after 2-3 seasons, I'll upgrade and replace the original version. If it's something I never end up wearing or I feel like it's not authentically me, then there's only a small loss there. For example, I tend to do a minimalist military / americana workwear lite look, and figured hey an MA-1should work well with this, but I've never owned one. It's a bulky cut and a certain look, so I got one from H&M for $40-60 and have worn it now for 2-3 seasons and really like it, so I'm on the lookout for something nicer like say that Lad Musician version.
Another point related to finding your grove versus experimenting, one technique that I've done is when I find an item I love and it feels like a certain look of what I'm going for, whenever I'm out looking at new stuff, I use that one piece as an anchor and ask 'will this go with that item?'. So let's say I have a Patrick Ervell Cadet sweater. I totally love the thing, and I only own one, but whenever I wear it I feel great and I think it really encapsulates the look of what I'd like to go for. So whenever I buy anything now, in my mind I'm thinking about if it would go with that aesthetic where that one item is the anchor piece. Now I don't only have 'one look' a la zoolander, but I have 2-3 very concentrated concepts. I also use this idea to cull the collection so if it helps me identify items that aren't really committed to any one style I'm going for which might be why I haven't used it much, so then I'll drop it to clean up the lines between the looks and make them more pure in a sense.
One final random thought here... When I was younger, I definitely tried out and experimented with a lot more stuff (clothing-wise he he), and while I like to adapt to the seasons or play with colors and textures, I do find something comforting in the familiarity of fit. So call me boring, but now when I find something that feels right, I tend to buy it in a stack of colors and fabrics. So I have 5-6 pairs of jeans, all the same cut, but different colors, washes, fabrics, etc. I found a t-shirt I love, I bought it in 5-6 colors an doubles of the basics. Etc. So even when I'm changing colors and fabric weights for the seasons, everything moves and feels the same.
Oh, one more thought. I mentioned the technique above about an anchor piece, both as a way to either make sure that new items coming in adhere to a certain concept, then the first point about if I skip that then using cheap low risk experiment pieces, and then the third point about taking the basic look and feel and 'experimenting' within it by getting the same feeling but with a bunch of colors and textures so it's more adaptable without having to add whole new items... The point I want to add here is another technique I've used to remove items. I generally organize everything as a color range, from black grey white, then colors from darker to lighter, etc, and also by textures from lighter to heavier, but sometimes I find resorting the data can find outliers. So if you group all one color together and step back, you may see you have way too much of X, or that you love your Y colored shirt but only have one so maybe get another one etc. I do the same thing with texture so see if I have too many spring/summer or fall/winter items.
Another technique I've used, which may seem a bit strange, is a forced rotation. So basically I have a pile of t-shirts, sweaters, button up shirts, etc and every day I have to wear something in the top 2-3 of the pile, then it's worn and goes to the bottom. This forces me to assess each item with roughly a 2-3 week period depending on the rotation of that item. If I find I keep not wanting to wear something and skip it for the others and it's sat at the front for too long, then it makes me aware there's something wrong with it and I stop for a second to look at why. In most cases it's something to do with the fit being off, or I don't know what to pare it with, etc. So the point here is that instead of shoving things to the back and letting them sit there, I make sure to actively keep looking at the items and assessing them. Sometimes I've reworn something and said ah now I remember why I got this, I totally missed out on wearing it this whole time, and other times I've said yeah I don't know what I was thinking, eh suck it up and sell or donate.
Anway, just some blabbing. Maybe I'm OCD but fuck it, we're on a clothing forum, you're probably the same way too non?