Winter Boot/Parka

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I'm moving to Chicago soon from California! I will be transitioning to a more office style role. I currently own Grant Stone Edward Waxed Tobacco and Grant Stone Antique Calf Oxford. I'm looking to get a pair of winter boots that will work for office work unless the Edward boot can work. Has anybody tested them in the winter with snow/ice?

I am thinking of getting unlined boot so it can be used for more than 1 season. I am eyeing Crockett&Jones Ross and Rancourt Freeman, but open to suggestions and ideas.

Additionally, recommendation for a parka? I am looking at the Veilance Monitor Down, Arc'teryx Therme, and Norse Project Rokkvi 5.0.

Thanks!