The Shoe Thread (esp: Red Wing)

Let’s talk shoes.

I’ve always been a: buy-a-good-pair-of-shoes-and-they’ll-last-you-forever type of guy. I recently asked my wife to take two pair of shoes to the cobbler for new soles. One place wanted $65, the other one wanted $55. That seemed like a lot of money to me. One of those pairs of shoes was over 10 years old; but the uppers are still in pretty good shape. I haven’t yet decided if I want to pay that much. The discussion below may help make up my mind.

So, what would you expect to pay for a shoe resoling? Is $65 excessive to you guys?

Fast forward a couple of days…
A Red Wing Shoe store opened up recently here in my area.

I had a pair of Red Wing work boots in my early 20s; I was excited when the store opened up… until I found out the price of their products!

I was looking for a good quality casual shoe (to replace above mentioned shoes)

Basically their starting price seems to be about $200; and about $300 for anything I’m interested in buying.
Am I just out of the loop? That seems like a lot of money for shoes. Have any of you ever bought Red Wings? Would you say they’re worth it?

And finally… are there any brand of men’s shoes you think are of exceptional quality and comfort with a good (fair?) price? For comfort I’ve worn Rockport, but I think those fall short in the quality category; and only seem to be getting worse.

Bonus points if there is a store in my area (Roswell, GA) or I can utilize my Amazon Prime.