My "winter boot" rotation is currently:
The Red Wing 4183, also sold as the "Rugged Classic" by J. Crew. CEE88 posted some pics of his:http://www.styleforum.net/showpost.p...postcount=1066
This boot works well because of the black rubber Vibram sole, the dark brown leather (which continues to improve with repeated wear and conditioning). It may look a bit too rugged for some, but I find it works with a variety of outfits.
The Waxed Canvas Hunting Shoe in Navyhttp://www.llbean.com/webapp/wcs/sto...tegoryId=65130
Some people may not like them, but I feel like the navy color makes these stand out. I've been wearing these like crazy the past two weeks with thick socks. It works very well. I may get a pair of the green for spring sized down so I can wear with thinner socks.
If you want something sleeker, I would say you should just do a custom order. Call up Leffot in NY and get a boot made. Something like these tan chromexcel on Vibram soles could work (the Chelsea model may not be ideal for snow; just have them made in a laceup or something)http://blog.leffot.com/2011/01/05/rider-boot-co-mtos-2/