Do gel inserts fix this?

They help at the ball of the foot and they do not change pitch or toe room, so they treat one of the three causes. They also take up space, which can make a tight toe box worse. Worth having, not a substitute for the right shoe.

Is a block heel always more comfortable than a stiletto?

For standing and walking, usually — the load spreads over a wider base and the ankle works less to stay stable. The height and the pitch still matter, so a very tall block heel is not automatically kinder than a modest stiletto.

Should I buy heels a half size up?

Only if the shoe runs small. Sizing up for room usually means the foot slides forward and jams into the toe anyway, which is the problem you were trying to solve. Room should come from the shape of the toe box, not from length.

The answer

My feet hurt after two hours in heels

The pain in a heel is rarely about how tall it is — it is about how steep the angle is between heel and toe, how much of your weight lands on the ball of the foot, and how much room the toes have. A platform under the front removes some of that angle without removing height, so a 90mm heel on a 20mm platform behaves like a 70mm one. A wider or rounder toe box stops the crush that makes hour two unbearable. And a block or a wedge spreads the load over an area rather than a point. Choose for those three and a heel becomes wearable for an evening; choose for height alone and it will not.

What answers it

ClarksAdriel Viola dress pumpComfort-built by a house that engineers footbeds, on a platform that flattens the pitch. This is the pump people keep after the pretty ones are given away.Buy on Amazon
NaturalizerMichelle classic pumpA round toe rather than a point, which is the single change that buys the most room where the crush happens.Buy on Amazon
DREAM PAIRSKitten-heel slingback pumpA kitten heel is the honest answer when an evening is long: less height means less weight thrown forward, and a slingback comes off and goes back on without a fight.Buy on Amazon
Sam EdelmanFelicia ballet flatThe flat that folds into a bag. Planning for the second half of the night is not defeat — it is the reason the first half can be in heels at all.Buy on Amazon

Prices live on Amazon, where they change hourly — so we never quote one. Every product here is a brand we would name out loud.

Pitch is the number nobody prints

Two shoes of the same stated height can feel completely different, because what matters is the drop from heel to toe rather than the heel measurement. A platform raises the front of the foot, so a tall heel can have a modest pitch. If a shoe is described as having a platform, hidden or otherwise, that is the detail doing the work — and it is why a 100mm platform sandal can outlast an 80mm court.

The toe box is where the second hour is decided

A pointed toe does not usually hurt when you try it on. It hurts once the foot has spread, which happens after an hour of standing and much faster in a warm room. That is why the shop fitting is misleading and why buying late in the day is genuinely better advice than it sounds. A round or almond toe leaves the room the foot is going to need.

Two thin straps beat one, and a slingback beats both

An ankle strap stops the foot sliding forward into the point, which removes a lot of the pressure at the toes. A slingback does the same with less commitment and can be slipped off under a table without a scene. Court shoes with nothing holding them on rely entirely on the toe box gripping, which is exactly the part you want loose.

Questions

Do gel inserts fix this?: They help at the ball of the foot and they do not change pitch or toe room, so they treat one of the three causes. They also take up space, which can make a tight toe box worse. Worth having, not a substitute for the right shoe.
Is a block heel always more comfortable than a stiletto?: For standing and walking, usually — the load spreads over a wider base and the ankle works less to stay stable. The height and the pitch still matter, so a very tall block heel is not automatically kinder than a modest stiletto.
Should I buy heels a half size up?: Only if the shoe runs small. Sizing up for room usually means the foot slides forward and jams into the toe anyway, which is the problem you were trying to solve. Room should come from the shape of the toe box, not from length.

Your turn

What should we dress next?

An occasion you cannot find anything for, or a product you want us to look at properly.