Below about three inches the foot stays in a position it can sustain, and above it the weight shifts forward onto the ball. No amount of padding changes that geometry. Every heel below sits in the sustainable range. Heel culture broke somewhere around 2020 and never fully reassembled, which pushed the whole market toward kitten heels, block heels and slingbacks. Comfort stopped being an admission of defeat.

A kitten or block heel spreads load in a way a stiletto cannot, and a snip or almond toe leaves room where a sharp point does not. Those two details predict comfort better than any brand claim. Comfortable heels are usually just well proportioned ones. Load spreading is a mechanical question rather than a brand question, and a wide base does it better than any amount of padding. Toe shape is the second variable and the more ignored one.

Low heels were the mid-century default, disappeared almost entirely through the stiletto decades either side of 2000, and came back through Prada and Bottega in the late 2010s. That revival was less about nostalgia than about a workforce that walks between meetings and no longer accepts a shoe designed for a car door. The category now sits somewhere between the 1950s original and a modern last with real padding. It is one of the rare cases where the fashionable answer and the sensible answer converged. That convergence is why the choice is so much better than it was a decade ago.

A last is the wooden form a shoe is built around, and it determines whether the foot sits back in the shoe or slides forward onto the toes. A shoe with a good last stays comfortable at a height that would be unbearable on a bad one, which is most of what you are paying for at the upper end. Look for a heel set under the centre of the calcaneus rather than behind it, because a heel placed too far back tips you forward. Leather linings mould to the foot while synthetic ones stay exactly as tight as they were on day one. None of this appears in the product description, so brand reputation is the practical proxy.

Buy the slingback or the low block heel and keep one pair of sharper shoes for evenings that involve sitting down. A heel you can walk five blocks in gets worn all year. The eight here are chosen on that test. One sharp pair for sitting-down evenings and one sensible pair for everything else is the honest allocation. Most wardrobes have this ratio backwards.