The coldest month of the year is usually February.
Global warming doesn't exist but if it did, you'd likely need boots, or use them even if you lived further south.
It's frustrating to look for boots that go from outside to inside.
ALL your problems solved (except global warming) with the Johnston & Murphy weldon cap toe boot ($170). The perfect mix between indoor and outdoor ~ you can walk from your car to the office and not be afraid your feet will be soaked. Plus they work with that suit once you're inside and have to run to a meeting.
Done and done.