In case anyone has time to talk me through this...

1.) Where I live, we suffer regular snow storms and long stretches under freezing temperatures. The populace lives in bizarre denial of this fact and fails in any way to deal with the snow (plow, shovel, etc.), leading to very unpleasant commuting conditions including unpredictable long waits in the cold wondering if the train will come.

2.) I want knee-high boots with thick soles BAD, REAL BAD. Even if this means dipping into savings. I am a bit traumatized after this past week of commuting.

3.) I have set my sights on a pair of knee-high, wool-lined, weather-resistant leather with thick traction rubber soles. Terribly expensive to boot
(Had previously set my sights on those Dolce Vitas Angie recommended, but I am not sure they would cut it anymore.)

4.) The question: I have to order these boots online but I tried on a similar pair in store but with a shorter shaft. I thought they were great, but slightly narrow across the toes. The leather seemed very pliable, so I think that might resolve itself. My better sense says never buy a shoe that doesn't feel good off the bat.
Has anyone had good experience with a toe box stretching out for your little toe and not looking weird after that?

5.) Alternatively should I cultivate a powerful sense of denial of the arctic weather like my neighbors?