Great question!
I think the biggest thing I've learned over the past four years is that it's OK take more risks because dressing ought to be an adventure and exploration as well as a studied, thoughtful selection.
I think there is a huge generational difference between those of us who entered the workplace before and after the mid-eighties. Prior to that point, dressing for the workplace was more about rules and image management than self-expression. If you wanted to get ahead in your career, dressing the part was a huge factor in the game as well as a way to deflect the casual sexism and discrimination that permeated most workplaces. Wearing that stupid suit with a pussycat bow and sensible heels put you into a uniform that resembled a man's business suit so you could be seen as a professional. A whiff of femininity could mar that cultivated image in a heartbeat--a lesson some of us learned the hard way.
The nineties set off an explosion of "I wear what pleases ME, and if you don't like it, too bad", a relaxation of workplace dress codes, and an explosion of fashion creativity through Internet blogging and fast fashion. We couldn't understand why our daughters thought it was OK to wear ripped jeans and see-through tops with stilettos to work, while they thought of us as hopelessly out-of-touch when we older women seemed concerned with "age-appropriate" outfits that would reflect our hard-won status in the workplace. Two different solitudes, each which had something of value to teach the other, but which too often just regarded each other with bewilderment, or, worse, with disdain.
That's exactly the bridge that Angie and Greg have created in YLF--a place where women under 50 can show us older women how to take risks and have fun with fashion without being dismissed or ridiculed for our concerns. And, I'd like to think we older woman can also offer some insight into why it can sometimes be wise to consider the impact unfettered personal expression can have on other areas of one's life and the people close to you.
That's why I think learning to see clothing as an essential part of my identity and being able to express myself more freely in my clothing choices is the best lesson I've received from YLF. The women on this forum have totally changed my attitude about the role fashion can play in my daily life. I owe all of you so much.