Cole Haan Women's Grand Ambition Pump (75MM), Black Leather, 11

This is THE most comfortable heel I have owned. There was zero uncomfortable break-in period (i.e. no rubbing, pinching, squeezing, etc.) and they've molded perfectly to my feet after just a couple of wearings. I wore them for the first time on a multi-day, multi-stop business trip and never felt the need or urge to take them off or change into flats, which I had on hand just in case. I've also stood in them for long stretches of time with zero issues or eventual lower back pain, be it walking around on hard, unforgiving surfaces or while working at my standing desk. These have become my preferred work heel, and I'll absolutely be purchasing additional pairs. The heel is slightly lower and narrower than other styles that I generally prefer - including Mylah, which I also purchased because of the blockier, taller heel - this is a far more comfortable style to me.