Kim, your idea of putting tick marks on your list is pretty darn smart. That should make it simpler to separate the "needs" from the "wants" - my downfall for sure. As soon as I read your post I realized that a replacement pair of Merrells should be near the top of my own list!
I've been true so far to my own version of SYC, which is to buy nothing else at all for winter, but to be open to purchasing items for spring/summer. Due to recent changes in lifestyle (retirement) and body shape (menopause) I am pretty much starting from
scratch to build an everyday wardrobe for warm weather. I didn't think I would be tempted to start spring shopping quite this early, but the 40% off sale at AT and AT Loft offered an opportunity that I felt was in the spirit of my original plan.
I ended up buying 3 light weight cotton blend cardigans, 2 pair of cropped pants (actually ankle length on my 5'2" self, but that can be remedied) and a rayon knit dress. Some of the items could be worn now since the Texas winter has so many mild days. But I'm committed to keeping them all segregated and with the tags on so that they can be returned in the next several weeks if I haven't found the perfect pieces to turn them all into outfits.
The bad news is that this unexpectedly early focus on spring items has pre-emptied my other goal, which I think is the original idea behind SYC - that is to experiment with re-mixing that items I'm currently wearing in new ways. <sigh>, maybe next week.