You know, I had to start a wardrobe from the ground up when my body shape and size changed significantly. Here is what I did, because I did NOT have unlimited funds. To say the least!! I was a barely employed writer at the time.
1. I bought a bunch of stuff at thrift and consignment.
2. I joined YLF and read the blog posts (archived ones, too) assiduously!!
3. I joined the forum and started slowly reading and posting.
4. I bought some more stuff at thrift and consignment, and quite a lot of stuff on sale. I tried a bunch of different styles - some things worked and some didn't. I chalked mistakes up to experience and tried to let it go.
5. I got a better paying job, at which point I also started buying a few higher quality items.
6. I paid attention to what i really wore and tried to put more money there. E.g. I bought pricier winter coats because winter is my dominant season and I am outdoors a lot in winter.
7. I started culling regularly as I realized things did not work.
Now I am not quite but almost on a one-in-one out policy. In other words, I have enough clothes to get by for most of my activities. I still have a couple of wardrobe holes, but not too many (at least for fall/winter). So now I am replacing less-than-perfect items with higher quality, more current versions.