For me it's been a series of moments - all with wonderful women involved - and a long process over time.
In my 20s, my very first boss coached and mentored me about what to wear on the job. She and I would go clothes shopping over our lunch break. This was the 80s and the time for women to wear power suits with big shoulder pads! We are still very close friends today, after all these years. I learned a few good tricks from her - but it was more about wanting to emulate her style and not about finding my own style.
In my mid-30s, I struggled through a divorce, restarting my career, and then a very lengthy layoff during the dot.com bust. I was pretty depressed. One day, a very good friend grabbed me by the back of my cordoruy pants, and said, "We need to take you shopping. You've lost weight from all the stress, and your clothes are falling off of you." I couldn't afford clothes for myself (I was struggling financially and the kids needed clothes more than I did), but I did go with her and choose a few items that actually fit. Otherwise, we spent time together just trying things on - not buying but having fun fantasizing about what I could buy once I got a job again.
What I learned from that friend is: No matter how down on your luck you are, no matter how little $ you have, you have to find a way to pamper yourself just a bit. You can't be a good mom if you're not first good to yourself. And that is it okay to dress nicely when dropping the kids off at school. I also learned from her that fit is very very important! And that often our brains still see fat, when the fat has been long gone.
The next phase in my process was a few years later. I was working and had $ and things were going well. A different friend - the one I refer to here as my VFBF (very fashionable best friend) was building her own career wardrobe and we'd have a standing date every other Monday night to go clothes shopping together. She has fabulous taste and I learned a lot from her. I also learned that what works on her (tall, pear shaped) doesn't work on me (short, hourglass).
Around that time like the others I started watching WNTW and reading up on books and educating myself about what fits, etc. But at this point I still owned no jeans. I had shifted to full-time telecommuting, and was very very slow to come around to the realization that jeans really fit my lifestyle better than dress slacks and khakis!!
So the biggest turning point for me was two years ago when I finally found "my" jeans!! And that led me to googling which led me to YLF!
