I have been wearing the same Red Wing Engineer boots for the last 12+ years and they have served me quite well because; #1) I am a daytrip rider, #2) I never purposely ride in the rain, and #3 they have been resoled and reconditioned by Red Wing, so they are as new.
That said, they are as soft and supple as glove leather, they do not have an additional layer or toe patch of leather to prevent wear from a shifter (they show no wear in that regard, though), they cannot be made waterproof and they lack the types of foot protection features of a proper or purpose built motorcycle boot with armor or additional reinforcement that any quality motorcycle boot should have to maximally protect a rider's feet in the event of a get-off.
BTW, I'm not into the state or storm trooper look of pants tucked into any sort of boot, which is simply a matter of personal preference regarding how I choose to present myself to the public at large.