I have the money, but I feel as though cordovan boots are neither the warmest nor the most weatherproof (even if waterproof, they'd become scuffed, dull, salted, etc.) Also, my leather-soled shoes are slippery as anything - I wouldn't want to even know what walking on ice with them is like.
It's just that I haven't gone through a winter season at the firm yet and so I don't know what men tend to do when the weather turns foul. Snow tends to be cleaned up quickly around where I work, I hear, but I still have about a five minute walk to the subway station and I don't want to arrive to work with wet feet when there's six inches of snow.
Maybe I can just use a car service to avoid the weather, but I don't know how quickly it can get from Brooklyn Heights to Midtown in the snow.
Also -- those boots I linked are on sale for $130, but Timberland is having a 25% off sale, and I have a 10% off % free shipping coupon that stacks. They'll be ~$90 (originally $150).