watch out for some of those youtube boot guys, the advice isnt always sound. One of the main ones recommended wearing clarks desert boots with shorts
I’m not an expert but a couple years ago made a concerted effort to buy a lifetime pair and I can endorse
Redwing classic mocs (recommend the moc toe since the cap toes wrinkle over time)
Danner mountain lights - these are great and perfect for the 9 months of winter and pseudo-winter in chicago (just takes a bit of care to keep the steel parts dry and rust free). Danner also has a great solid warranty and return policy
I’d stay away from clarks because while they’re quite comfortable and look good, they fall apart at like a sneaker rate in my experience