Once I was old enough be out of school and working full-time, I was happy not to have to worry about what "everybody else" was wearing. Where I worked women wore either skirts, dresses or else pants that were not as casual as jeans. At the time, they weren't "dress" pants, but they were dressier than what one would wear out and around outside of work.
I like simple and feminine-feeling clothes, so since these were being worn at the time, I often bought "pants sets" (not to be confused with pant-suits) that involved soft-fabric pants with one or another kind of long, flowing, top that matched. As long as I was careful not to get something that someone, say, over fifty would wear I didn't have to worry about looking matronly because at the time I didn't have a matronly build. In fact, it was because I have a very small frame and, at that time, weighed in the 106-116 lb. range that I aimed for clothes that were feminine, professional looking, and didn't run the risk of coming across as "cutesy". (When you're really small and have a young looking face on top of the fact that you are, in fact, in your early twenties; you don't want to come across as if you're embracing the whole "little-girly" thing.
Also, at that time, mid-calf skirts were around; and contrary to the believe that small women shouldn't wear long skirts, I found that a lot of people didn't realize how short I am because with heels (or platform shoes of the 70's) combined with one, long, "visual fiield of color", it looked (at least I thought) OK. Besides, I'm not under 4 ft tall or anything like that. I'm 5.2.
At the time, jackets/blazers came in any number of fabrics, including "synthetic" (aka one kind of polyester or another). Some of that was worse than some other. It depended, I guess, on what the mix of "synthetic" was.
In any case, whether synthetic, linen, wool, cotton, "faux suede", or whatever else; I had a lot of jackets.
On the one hand, I care enough about clothes to at least hope to look my best. On the other, I don't want to be thinking about them the whole time I'm wearing them. So, when I was working fulll time (but also now sometimes) I found that a simple skirt with a simple, comfortable, top under a jacket felt feminine, required no thought, and looked pretty much OK anywhere.
Something else that I liked to wear was simple, pull-over, dresses that were essentially long jerseys or long sweaters. Effortless, so I liked those.
Being single and working, and being someone who took care of my stuff, I usually had a few coats of one kind or another, depending on the season.
What I wore when I wasn't working depended on where I was going or what I'd be doing.
In recent years I found the book, "Dressing Your Truth" by Carol Tuttle (who is a woman who has "a whole deal about knowing your type, beyond just the book about clothes). Other than look at some of her videos about clothes and types, and other than reading that one book, I didn't pursue any of the rest of whatever she's got going with books, videos, store, etc. However, it was interesting to read the book, and I kind of figured out that, for the most part (and at least since I got past my teens), I've always very much someone who dresses for what's right for me and what feels most comfortable, rather than allow trends make me abandon the kind of clothes that I like.
That doesn't mean I won't abandon some things that are out-and-out out. It doesn't mean that I don't like fresher versions of classic clothes. I just mean that even when I was young I wasn't about to be a slave to either fashion or clothes.
Once I quit working full-time, had three little kids, and sometimes took short-term or freelance projects, I had to re-think a few things and aim for clothes that were more all-purpose (while still "being me").