If you wear heels regularly you are bound, sometimes pretty frequently, to get some variation on this question:
How do you wear those heels all day? Aren’t your feet killing you? I could never wear blah, blah-blah, blah, BLAH!
I contend that heels can be comfortable depending on the height, style, maker and where you are going, so that there is a heel for you and you can just stop denying yourself. And they are so pretty that why would you want to?
My friend wrote to ask me:
The only thing I want to know is..How to wear heels when they make your feel hurt.. Lol.. I am wearing all those sketcher biker style shoes and sandals with no heels .. I love my heels, but they all hurt to wear…
Dear Friend – I’m sooo happy to help and spread the heel-lovin’ joy.
First – make sure you don’t have any foot, ankle, knee problem that maybe causing any pain.That done, here is my shoe-sie advice
A simple addition that could help are the gel inserts that go under the ball of your foot. These do provide some cushioning, are inexpensive and can even help your shoe fit better (especially if you are like me and many of your shoes are a bit big).
Next – choose your height wisely. How high are the heels that are bothering you? You don’t have to get 3″- 4″ heels to find some pretty styles.
I know this is going to sound trite but the higher-end brands really do have engineering that makes a difference. I can walk much much more in a pair of Jimmy Choo’s or Manolo Blahniks than in a lower height, less expensive brand because of the workmanship and, frankly, the architecture of the shoe. You put them on and the difference is amazing. Also the double-strap Miu Miu Mary Janes that were just out have an internal platform that was so cushy I couldn’t believe it.
In terms of styles, I would look at a Mary Jane platform because it is classic and it will help hold you in place. An extra bonus is if you get these because Cole Haan is doing a line of shoes with Nike Air cushioning. They are so classic looking – maybe I need a pair too. Hmmm… for research, of course. Wait, where was I?
Oh, yes – I would also look at a chunkier heel rather than a a spindly stiletto. Heels with built-in platforms give you the height but your foot isn’t really going as high as it looks. And find a brand that fits you well. Nine West is one of those brands for me. I have had consistent good luck with their styles. The sizing is right on for me and I can wear their heels all day.
Aerosoles are also a stand-by brand for comfy heels – I just tend to find their styling hit or miss for my tastes. And then there is the fact that you can’t resole them either. Which, if you like your shoes and invest in them, you don’t want them to wear out too fast.
I would stay away from wedges because I tend to find that my ankle goes out in them and you can tumble a little because the sole of the shoe doesn’t bend. Right on the ground
So, I would find a good height and style and then invest in good quality. By taking care of them with proper maintenance, they will last you a long long time, you will actually want to wear them and that is where the true value will be apparent.

Cole Haan Dalya Air Mary Jane