Deborah, I joined just after you did -- in May, 2011!
And what a ride it has been.
I arrived with honestly very little in my closet. I had just lost a lot of weight. What I did own was almost entirely bought at thrift or consignment. I knew I would need a period of experimentation to figure out my style and I did not have a lot of money to do that!
I'd always defaulted to "classic" but feared that classic equalled boring and dull. I tended to wear a lot of blues because I knew I looked good in blue -- but feared that was a bit tame. I tended to wear jackets with jeans and boots because it fit my climate and lifestyle -- but wasn't sure of fit or proportion and often got that wrong. I had always loved an androgynous look, and had always loved short hair -- but had grown my hair for a more "feminine" appearance for a while.
So I experimented for a while with draping, arty looks, retro, even some steampunk elements! I continued to buy at thrift and consignment for about a year because I had a very small income.
Then I got better paid work and began to build my wardrobe more mindfully. Even so, I made a ton of mistakes! I bought and purged, bought and purged. It seemed there wasn't any other way for me; I just have to learn from experience.
At long last, I'd say I'm pretty close to having an excellent working closet, one that works for my life and expresses who I am. And-- lo and behold -- like you, I find that I have pretty much come full circle. Back to classic -- but with a heavy dose of "modern" and "minimal" added to make it feel current and fresh. Back to my blues, because they really do suit me! Back to jackets and jeans with boots. Back to my short hair.
I own almost nothing that I had, pre-YLF. One dressy skirt, that I had altered after my weight loss. One simple black jersey dress that was a gift from a friend.
But I fully expect to own a lot of the items in my current closet in 3 years' time. The quality is higher, the happiness factor is higher, and I have many items now that you'd have to pry from my cold, dead hands to get away from me.