I’ve been wearing steel toe boots for work for the last 35 years. It’s not necessarily the boot as much as it is the insole. You can always buy a high quality insole and replace what comes with the boot. Redwings will last a long time but hurt like he!! breaking them in. My personal favorites for comfort have been Justin and Ariat. I’ve worn Ariat for the past 3-4 years I guess. Comfortable but they are worn out in a year, with 5 days a week worth of wearing. Of course work buys me a new pair every year so it doesn’t matter much.