Put your foldable flats back in your bag: A night in heels shouldn’t mean you have to hobble home. Before going out, tape your third and fourth toes together using nude or clear medical tape (the flexible kind). This helps take pressure off the ball of the foot. (A bit of biology for those who are interested: There’s a nerve right between these two toes, and the tape minimizes any strain.)
Size and shape: When was the last time you had your foot measured? If you’ve had children/gained or lost weight/or just plain can’t remember, it’s time for a recheck. Too small and your foot doesn’t sit well in the arch. Too big and it slides forward. The best fit will nicely hug and support your arch, and it definitely shouldn't hurt. Also, opt for wider toe boxes for best comfort and less long-term injury.
I’ve heard people argue that my new, near-daily ritual is ridiculous, that no shoe is worth that much pain or effort. But how different are heels from other small rituals we undertake every day, such as applying makeup? The payoff in terms of the confidence I feel when stomping down the street in a pair of killer heels is worth way more than the extra 30 seconds added to my morning routine.