So, yesterday I was at the Burlington Mall (a big mall with a poor-man's Nordstrom -- very small shoe dept). Anyway, I tried on a bunch of low black boots -- chelsea and chelsea-like. If you've seen a few of my recent posts, you know this search has caused me a lot of pain.

I realized a few things yesterday. First, the term "chelsea boot" has many interpretations. Second, the interpretation I have had in my head is really the one that is not going to work for me. I cannot believe it has taken this long for the penny to drop. What I love in theory is the flat pull-on short black boot with the roundish toe. But, I really do not love a round toe on a flat boot. (Anyone remember the Frye Philip shorties that I consigned for this very reason?) I nearly had a migraine by the time I realized this. (I felt quite a bit like Cinderella's step sister, trying to force myself into a style I am wholly unsuited for.)

I also realized that I do not want to spend more than $250 on booties, and less is better. I am hard on footwear, and I like to change things up every season or two. It does not make sense for me to spend extreme amounts on luxe footwear. (I did try on a pair of AGL "Cherry" booties that were amazing at $450, but really, the likelihood is way too high that I would be bored with them by February.) I'd much rather find the most comfortable mid-range footwear I can and wear it for a season or two, pass it on, and replace it. I'm not into longevity for my feet, and I actually have been quite happy with Zara and Topshop footwear, which lasts just about as long as my love for it does.

Ultimately, I brought home a pair of Madewell chelseas: the Joni bootie, very comfortable, slightly Western (and the ankle opening is not nearly as big as it looks in this picture). The Western styling gives me a little pause, but I really like how they look and feel on. Still, there are a couple from Zara I also have my eye on, so I am leaving the Jonis in the box until the others arrive.

I'll probably be looking for feedback once they are all here, but for now I wanted to share the learning. It's been a painful but productive journey.