As far as I'm concerned, you're way ahead of me at the time when I was a new mum - style wasn't part of the equation at all. A lot of factors were to blame, but framed by two main ones: my height - of course - which made shopping difficult in general, especially for the transitional body, nursing, need for comfortable clothes, and a lack of sense of style because of height difficulties if nothing else. Not to mention that I had no support in the form of YLF who will hold your hand.
I think Pinterest can easily turn into counterproductive tool, that was at least a case with me, I got overwhelmed very quickly just looking at other people's boards. And partly because I've learnt my lesson from bookmarking (good, old-fashioned bookmark for keeping URLs) zillion links for all the recipes I will NEVER make, but can only feel frustrated because of it (but really, how many meals will I realistically need to make in my lifetime? So, how will I filter through all that food… how much TIME alone it will cost me to rummage through all that.) I have not used the Pinterest to hone my style. At least not yet. But I can also see how it can be very helpful - it did help me a lot to see the trends I like in making some decisions about our future house, but for now I leave it at that. I occasionally pin the look which really, really speaks to me, but I have detached myself from analysing my style through it yet. I like it and I leave it at that.
Instead, I am working through my own, existing wardrobe. A few weeks ago I wrote about my need to go simple in terms of clothing and I've had a blast since then. I literally tune into every piece I wear and have in the process started becoming aware of what I like and dislike, what feels most like me and why, down to the seam and cut. I still wear imperfect things, but I learn from them, and there is a reason why some survive in my wardrobe. Some I ditch without thinking twice. The things I love come from all price points, the more expensive ones from sales - but can you tell? I don't care, all I know is I LOVE those pieces and WHY I love them. It's a journey. And it's fun. That's what it's all about for me.
I hope it makes some sense to you