I suspect the problem is that the sole is very stiff, so all the strain of the shoe bending occurs at that one spot. you might try boots that are either less stiff in the sole, or that dont have the stitching running across that spot, for instance a single piece or if multipiece having the stitching up near the middle of the arch.

...worked wonders for me, when I had 2 jobs on farms: one in the mornings, feeding, rotating, and mucking out stalls/fields on a horsefarm, and in the afternoons as a fieldhand on an organic vegetable farm. I never paid the $100+ that you see advertised, but probably spent between $25-35 at a hardware store for pair of calf-high mucking boots. My feet never got wet, and they were tough enough to withstand being stepped on occasionally by the Belgiums. Love the blog, thankyou!

My granddad, who was a tulip farmer used to wear traditional Dutch all-wooden clogs all year round on the farm. In the winter with woolen socks and straw for warmth. These one-piece wooden shoes are pretty much waterproof, so your feet won't get wet. And they work as safety shoes too!

Modern farmers probably swear by a pair of wellies.

I can attest to the fact that that stuff is rather good at reattaching soles to shoes. I used it some 20 years ago to do precisely that and the repair was good as new and lasted for quite some time.

I would absolutely recommend it for re-attaching soles, but not repairing damage to the top of the shoe. My dad wears Bean boots, so something similar to that would be an option. They have very flexible soles and the main foot area is rubber, which might hold up longer. For cost, I would second the recommendation of insulated rubber boots.

Wow, it sounds like you all have a lot of experience with both shoes and goo. Rebecca's suggestion makes a lot of sense --- work boots do tend to have very tough soles so that you won't wear through them. I'll have to check out Stephanie's suggestion too --- I've never had luck getting rubber boots to last more than a couple of months, but maybe special mucking boots are the solution? Fascinating about the clogs --- we had a small wooden clog when I was a kid, and I always thought it looked highly uncomfortable, but I can see how it might be more utilitarian if made right.

If we need to reattach soles, sounds like we should go back to shoe goo --- thanks for the firsthand experience, Shannon and Brandy!

Not all rubber boots are created equal. Boots being advertised as "rubber" can be made from modified natural rubber, injection moulded PVC or polyurethane ("PU") and maybe others. All rubbers (elastomers) eventually break down under the influence of UV and other outside inflences, because they are somewhat poreous. I think natural rubber is the most tear resistant, but tends to break down easier. Some plasticizers used in PVC have possible health issues. PU can be very elastic and tear resistant, but might be more expensive.

When looking for leather boots, you should look for work boots where the front of the foot is covered by a single piece of leather without stitches. Of course leather needs more maintenance than rubber. Boots with steel toe caps will aleays tend to tear just where the toe cap stops, due to the difference in flexibility between the materials.

Have a look at motorcycling boots. Most of those have a zipper to the bottom so they are easy to get in and out of, and they have a waterproof liner (gore-tex, running behind the zipper) these days. Military surplus boots might also be an option to look at.