Shoes! Shoes? Shoes...

I've always had a difficult relationship with shoes. They hurt my feet. All of them. Even the most comfortable shoes on the planet will give me blisters, and for a variety of reasons all shoes I wear MUST conform to the following standards:

They MUST be as narrow as possible, preferably with a pointed toe.
They MUST end below my ankle, unless knee-high.
They MUST weigh as little as possible, preferable to not be felt on my foot all all.
They MUST support my arches well.
(and for dress shoes, mostly) They MUST have a heel.

I went to a podiatrist a few years ago because I lost all feeling in my little toe, and after an exam the doctor asked if I've ever done ballet. "yes", I replied carefully, "but not for a long time." Do I wear high heels? "yes," I said just as carefully, "daily since I was 12 years old."

It turned out I have foreshortened Achilles' tendons, developed through years of heel-wearing and intermittent dance training. This mostly manifested itself in unbearable leg pains whenever I'd put on flat shoes. Trouble is, I work on my feet 10-15 hours a day, and in flat shoes. I'd love to have some heel, but they suck for climbing ladders.

The doctor suggested I slowly stretch out my Achilles' by having heel lifts in my work shoes, which seemed like an interesting idea, but I went cold turkey and wore nothing but flats for a few months. The pain was unbearable. However, now I can effortlessly switch between flats and heels with minimum pain.

Which brings us to work shoes. Last week I discovered that my shoes no longer gave me the requisite support (as manifested by terrible pain in my arches and lower back) after running around from 9 am until midnight. New shoes it is, but which ones? Given the above requirements, I can't very well use standard steel-toe working boots (too heavy), clogs (not secure enough) or even Doc Martens (wearable, but too ugly)

Over the years I've tried several brands of work shoes, from LLBean mocs to Timberland hiking shoes (which is where we are right now.) Timberlands cost $100. The last pair was bought a little over a year ago. $100 per year seems like a lot sometimes. But I suppose, not until you see what I DO with said shoes. Behold, the gallery of my past 3 pairs of work shoes:

Old Timberlands (when they were new)

And this is what the Timberlands turned into after a year and a half of daily use:

So those became my "spare" shoes and I used these Pumas for a while, in-between other shoes.

But apparently, Boston winters and WEARING the shoes is not good for them...

So I bought new Timberlands, in the vain hope they will last longer than the other ones.

Only to be severely disappointed 14 months later:

I ordered new shoes. I am trying a whole other tack - dance shoes. It's quite possible they might give me the support I need, and even if they die after a few months, they are only $30.