Comfortable high heels exist, but finding them takes more than choosing a pretty shape. Most heel pain comes from a few predictable culprits: a steep heel, a narrow toe box, thin straps and a poor fit. This guide explains each one in plain terms so you can spot trouble before you buy. We also round up six heels from our catalog, from a 2.5 inch kitten sandal to a block heel with an ankle strap. Every pick is a kitten, block or chunky style, since a lower or wider heel is usually easier to wear than a stiletto. We did not test these shoes hands-on, so we stick to what each listing says. Use the notes on who each pair suits to narrow your shortlist quickly.

Start with heel height, because it changes how much weight lands on the ball of your foot. A lower kitten heel keeps your foot closer to level, while a taller heel asks more of your forefoot. Next, look at toe shape. A square or rounded toe leaves room for your toes to spread, while a sharp point squeezes them together. Then think about how the shoe holds on. Ankle straps and slingbacks secure the foot, while mules and loose pumps can slip. Finally, check the sole and insole details in the listing, and add a cushioned insert if the shoe feels hard.

Fit matters as much as style. Try heels on in the afternoon, when feet tend to be at their fullest. Walk on a hard floor and take a few stairs before you decide. Break new pairs in at home for short stretches. Keep a foldable flat in your bag for long events. If you have ongoing pain, numbness or a known foot condition, a podiatrist is the best person to ask. With the right shape and a realistic plan for wear time, a good-looking heel doesn't have to hurt.