Such good questions and responses! The last few months is the first time I've consciously tried a style refresh. Along the way, I've had a few narrow escapes from trying too hard to make a trend work for me.
In the past, I've always SYC quite a bit, and tended to buy things when I discovered "holes" while putting outfits together. Ironically, that's made me somewhat an impulse buyer: I have an awesome outfit waiting in the wings! Fill that hole right now!
So what unfrumped said about being intentional and getting the foundation in good shape first really resonated. For me, footwear was the single most important item; my closet is full of 1940s and 1940s-inspired shoes that work with my clothes, but are hard to style in more fashion-forward ways. Pointy toes and ankle straps were my first big step. Then oxfords, calf-high flat boots, and white sneakers followed. And in the last two weeks I've finally added booties. I'm also working on upgrading my basic leggings/stretchy pants capsule, since I spent so much time in it last winter. The discussion on making short tunics/long shirts work has been extremely helpful.
I also noticed that I'm feeling drawn to trends a year or more after Angie first identifies them. Like Chelsea booties. I was somewhat appalled to see how old her post was when I looked it up! And the whole trend for booties with skirts and dresses, which was such a weird look two years ago, and I'm finally really wanting to try. The responses here encourage me that being a late adopter is just fine. And good thing, too, because I finally found my booties. I love them, I'm wearing them now for the first time, with a dress no less, and I'm thrilled.