Great post Natalie! I saved it to read with my morning coffee. Lovely! You've gotten some great responses. I have a pretty small wardrobe, but I've been on a summer buying spree since that's my dominant season. I'm actually invigorated by a good purge, so it's hard for me *not* to cull when I start getting that overwhelming feeling of my closet getting out of control.
I'm on a learning curve too. I buy clothes to experiment with different things to see what I like and what I keep reaching for over and over. I ask myself what I *don't* like about the things that I'm not wearing so I can avoid making the same mistake again. I don't think I ever want my wardrobe to be *finished*. I would rather have some blank space that is open for new possibilities. At the end of each season (such as they are), I only aim to keep the pieces I have really loved and look forward to wearing again the next year. By cleaning out the items that I feel *meh* about, I have some buying to look forward to when the season rolls around the next year. Sometimes they're perfectly fine items, I just feel done with them for some reason. So off to the thrift store they go, from whence they came, lol! (BTW that cracked me up about you rescuing your dress from the consignment store mannequin!)
So, to your question, I think you need a lot of career wear, and your good quality things will last you a long time, so no need to scale back there, maybe one-in-one-out? Your MOTG category is a little lean, so that might be a fun area to concentrate on. You won't need a ton of clothes for this, but I'd branch out from the formulas that are working well for you (and DH likes) and add a few pieces. Sometimes a pair or two of neutral shorts is all you need to exponentially increase your outfit options.