Yeah that’s a tricky mix of criteria—maybe take pics if weatherproof boots/shoes that look/are comfortable, and run them past your supervisor so you don’t waste money. I can’t imagine they want you to get frostbite so those chukkas or Timberlands will pass muster. I’ll add these gore tex ones that are definitely waterproof.
Measure your feet at a shoe store, with that device. Braddock?