Aw, Natalie! Both of these looks are wonderful and suit you beautifully. There is nothing wrong with having a few different styles, and you certainly have the need and skill for both simplicity and matchy-matchy ALGO!
I have to say, it cracks me up that you have a small collection of books on simplifying. My house is a similar disaster - only one kid, but he is messy and active in sports so there is gear everywhere, and DH and I both work really stressful jobs, and we have five pets that are always shedding, barfing, kicking litter around, getting in the trash, or tracking in dirt. And none of us are particularly orderly or neat. We have piles of unread New Yorkers and Sports Illustrated and InStyle. Because we are just always on the go, sometimes the house feels like a way-station. Just yesterday I told DH I was going to go nuts if we didn't get the house clean before my parents come and I have my surgery. On the other hand, there's so much I'd rather do, and cleaning quickly becomes my last priority when there's a better offer.
Wardrobe-wise, I think you take the time to figure out what truly makes you happiest and stick with that. Sometimes - at least for me - it's hard to differentiate the immediate gratification of buying from the joy of owning and using. It's like the difference between being smitten in love and the post-marriage long term commitment.
Also, I know you and I can both get caught up in the hunt and obsess over an item (*cough* polar bear clutch). That's no longer fun for me, and I am trying to learn to let things go before I buy them, rather than after.
One thing I see is that your love of matchy means you collect entire sets of things like the Target collabs or the BR outfits. Do you enjoy that kind of collecting or do you do it out of compulsion and FOMO? I know that I bought those patched Mother jeans the other day partly out of FOMO panic - I looked online and saw they are sold out, so I immediately started stressing that I would regret not getting them. But that kind of shopping doesn't always result in a happy purchase for me.
So,, if collecting sets really makes you happy, then maybe allow yourself to do that to appease your matchy love, and simplify elsewhere. Your stuff should lift you up, not weigh you down.