B-mom, I have been surprised at how long it has taken to build a functional and stylish wardrobe. I've been following YLF for nearly two years, and in that time have slowly replaced just about everything in my closet, with *many* missteps along the way. My practice now is to send anything that seems to have been a misstep to the consignment shop and not let it sit in the closet accusing me, and also to take things that are almost right and get them tailored.
I had trouble at the beginning with assembling "infrastructure": the pieces that aren't exciting to invest in but that make everything else work. The right white and black camis, for example; underwear that doesn't peek over your waistband or produce VPL; a small assortment of tights. Now that I have those items in place, getting dressed is a whole lot easier. This year I have to replace my plain black dress pants -- definitely not a thrilling purchase, but one that I know will hugely multiply my outfit options for work.
I don't know if any of this is helpful to you, but just wanted you to know that it does take time and isn't necessarily a smooth and straight path. Hang in there!