Such a good question. I had a couple of friends over for a back yard visit a couple of weeks ago. Both tend to like to have very high quality items and aren't afraid to spend on clothes, shoes, and bags. One I would describe as a mostly conservative classic leaning to preppy dresser. The other is classic and somewhat conservative, but not preppy. She loves bold jewelry, bags and statement shoes.
Both of them had put on some weight during the pandemic (who didn't! But I think I have a point here, so I mention it).
The more "preppy" dresser came in dark straight jeans, very nice flat sandals (not a comfort brand but can't recall what they were) and a plaid shirt over a tank top. The other was in a new midi dress in the perfect shade of blue to go with her eyes. When I gain that kind of weight, I tend NOT to want to shop, finding it so hard to find anything that fits and makes me feel good. She insists on keeping a fashionable closet no matter what, and frankly, she has good instincts and always looks great.
I think I was in black jersey knit culottes and a sleeveless floral blouse -- both of which I've had for a few years.
When we met, the three of us were probably among the 'best dressed" in our workplace, and that may have drawn us together - although we also worked together, so were going to end up in close contact anyway.
Although we sometimes shop together after a brunch date, we seldom "talk" fashion otherwise. I mostly prefer to shop alone, but I do have one other friend that I have shopped with from time to time, and she was actually behind a few really good purchases.
Most of my fashion "dialogue" is internal. I take inspiration from others' style journeys here, and am trying to figure out where I am on my own. Dressing hasn't been much fun since I piled weight on over the last ten years or so, and I felt I lost an important avenue for self expression. Trying to work my way back to fashion as fun.