Sensible option: Eastland, $115 
Splurge option: Oak Street Bootmakers, $326 
Why dad needs it: Your father taught you how to be a man, and while you still might be trying to figure it out, at least you know about boots that make you look like you know what you're doing. When he's tromping around the yard or putting in work, make sure his feet are protected and look good while he's doing the manly shit that one day you will be able to do.