As of this moment I am wearing a pair of black vans skater shoes that I bought around 2005; not because they are stylish (they are marred and muddled with white primer paint) but because they are comfortable and dry and to give my standard issue winter boots a chance to dry out. At the time of purchase I figured I'd try out skate boarding, but gave up after failing miserably after a few basic tricks and deciding I'd save myself the future injuries and surgeries.
Normally I'd be a big proponent of Merrell shoes/boots, but it seems after they stopped being made with American Pride, and started being made with Chinese/Taiwanese sweat I've lost faith. My first pair of Merrell Mocs were bought in 2004, and lasted me until 2011-12, then I bought a replacement pair, same kind/different color/different country, the life span was significantly less then half of the last, the wear/tear/abuse was the same, only difference was country of manufacture, I've almost but not quite lost faith in the brand. It can't be a coincidence that the first pair was made in America and lasted close to a decade but the second pair manufactured in china lasted a fraction of the time. I'm still willing to buy a pair if the price is right but I'm doing research to branch out and put my hard earned money and trust into another brand/country of manufacture.
As of late I've been wearing my standard issue winter desert combat boots because I never wore them in the service and they are water proof and warm (but they roughly weigh about 6+ lbs/pair), however because they are pretty much my only waterproof pair of footwear I have to wear them on a continual basis for work, disallowing them time to dry out, and they stink to high heaven because of the lack of breathability. I was perusing black friday/cyber monday shopping for replacement footwear, but I'm not going to shell out $250 for a pair of boots just to pay for a name.
Instead of providing pictures and links to footwear of various shapes/styles/brands, I'm going to plug super feet insoles, because no matter the brand or type of footwear I decided to spend my hard earned monies on, those insoles have provided me 1-2 years of continuous comfort. They seem rather pricey compared to some of the Dr. Scholls inserts, but like Vibram soles are good for atleast a year of wear and tear. They run from 20-30 bucks for a pair of the insoles, but after about 30 days of breaking in will provide good support and shock absorption for atleast a year. I'm sure you could get away with $20-$30 shoes equipped with these insoles and get away with a year of comfort. Mind you the soles might outlast those walmart $20 clunkers, but after the break in period the soles pay for themselves in overall comfort and durability.