Depends on where you are....
In Toronto, it'd focus more on waterproof boots than -40C comfort. We get slush, rarely mounds of snow. One or two massive dumps of snow a season...otherwise rain, slush and general slipperiness.
Pretty much any boots are good...my Danners are going strong after years of winters/games/etc...
For pure warmth...the felt "pack boots" with a draw string top are hard to beat. Super comfy. These are the ones I go to when I'm shoveling the drive on a weekend morning.
Despite how goofy you look...mitts beat gloves every time. Or lighter weight gloves with a mitt shell.