Casey, I went through that phase not too long ago (I am 25) and also took a lot of advice from WNTW, so I totally know what you are going through.
I don't mean that they should "chase every trend," but that they should at least update their concept of what is and is not suitable. Fashion evolves and changes and yet their ideas seem to stay the same. "Classic" does not mean static. New ideas and "trends" have the potential to BECOME classics. Think about it. Every classic started somewhere. One thing I adore about our Angie is that she can own up to it when she changes her mind about something, and she can accept new ideas as they come along.
Having been in your place, I have a few thoughts on how their idea style influenced me in my early 20's.
-First of all, they drilled the idea into my head that money=quality, and quality=essential...as if I would look like a total slob and not get a job because I looked "cheap." So at 22 years old, I thought I had to spend lots of money and get high quality pieces so they would last a long time and I would look presentable. Well guess what. Three years later, I am a completely different size and shape, and I couldn't fit into those clothes if I tried, and I realize what a mistake I made spending so much at such a young age when my body was going through so many changes.
-Second, they really like to emphasize sophistication. In many ways this is understandable. Sophistication is a flop proof formula for being stylish. However, is it the ONLY acceptable fashion persona? Definitely not. And I would go so far as to say that for most 20somethings, it isn't even ideal. It's awkward and constricting. This is the time to experiment and be daring and have fun with clothes! It's better to embrace that while you can. I do not have a sophisticated style and I am happy about that. Maybe once I'm (much) older, I will, but for now, this is my time to go crazy. If I end up looking back and cringing, that's okay. I would rather cringe than end up regretting that I didn't take full advantage of my freedom and youth. During my early 20's, I would avoid all kinds of trends that I secretly loved because S&C told me to, which was so frustrating. Once I found Angie and YLF, she sort of freed me from that.
-From a practical standpoint, I always feel as though they don't really consider the needs of the individual person in a realistic way. Putting a SAHM in strappy 4" wedges because they are "stable" and "comfortable"? In your dreams. The SAHMs of YLF know how it's done, and that isn't it. Climate and location also rarely seem to figure in.
So having said all that: You're right that the show is for people who are really starting from scratch, so getting them the basics is important. Some of them are just clueless, but not always. A lot of times they do care about how they look, they have the right attitude, and they come in with a strong aesthetic. All they need is some adjustment and tweaking. I just don't feel like they always take individual people and lifestyles into account as much as they should. They think they do, but everything really ends up being different variations on a theme.