Rag and Bone “Harrow” bootie, Banana Republic jeans, Gap sweater (similar)

I’m just going to put it out there and say that i’m bad at San Francisco weather when it comes to shoes. I’ve mentioned this issue before: that I seriously don’t know what to put on my feet when it’s too cold for flats but too warm for knee-high boots. I was seriously hoping the solution were these Rag and Bone booties. With their lower cut front and reasonable heel height, I had hope! But, after taking these pictures and seeing what they truly look like on, I couldn’t justify the price tag. See below for full reasoning.


The side view is where a lot of the issue lies. My feet look like boats, I kind of feel like a clown, and I don’t like the shape of the shoe or the heel (the way it kind of curves in at the back). Comfort wise they weren’t as comfortable as I would want for walking the city streets (i’m spoiled after my Tieks), and the leather would have taken some breaking in. I also wasn’t a fan of how high they came up on the sides of my ankles.


Material wise, the leather is great quality and the black is gorgeous. The details like the wrap around are sensational. I don’t particularly care for how they wrap straight across the front ankle, but I could get over that.

All in all, these looked great with black tights and a little skirt but not so good with jeans rolled up or tucked in. For $500+ they better look amazing with everything, so back they went. Have you tried the booties? I’d love to know what you wear in these sort of weather predicaments!