This is a great post even though there may not be a "right" answer.
I have been developing a better balance on what is working and what is not. I'm happy for YLF to "open my eyes" to trying new things because I have had a lot of fun with that. But I also learned that it was not fun to go in to many directions at once, and also that I needed to relax and be happy when I had some items and outfits I really liked and not worry that I was "out of date".
I think there was a tendency for me to feel a pressure to " buy and try" on YLF at a rate that was too fast for me, not that it was intended, but I was just susceptible. I was able to see ways to improve style and saw lots of goodies but there is only so much I could incorporate and still develop at my pace and also, still be "content".
It was like learning a new language, and I had to learn that a lot of background new, and trend, and fun, and different was there, but I did not have to take it all in or use it all. So it's not wrong or bad, but it's like being at a buffet when you need to watch what you eat! Also I became aware that there were so many new options all the time, and that thankfully as Angie has noted, more different styles are going on at one time than maybe has been true in past decades, that you aren't really as likely to be totally "in" or "out" unless you've really been in seclusion!
Now one of my issues is that as I became more intentional in finding things I liked for updating, I liked them myself for my own style, and then found I might still like them after 2 or 3 years! Because, of course, I chose them in part for real reasons such as body type, lifestyle needs, comfort level, and "sugar eye" for certain things. So now I have a "new problem" of being more aware of updating but also more in tune with what I like, and need to balance all of that in a way that is fun and not frenetic.
One of the tradeoffs I have to watch out for is "time" vs. "new". Perhaps because I'm not a "natural" at style, some new things may be harder for me to figure out or put together, even if I like them, and if I get too much new, I'll spend too much time churning wardrobe outfits and worrying about proportions and having too many choices instead of getting dressed efficiently and happily. That was a big "aha" for me.
