
Aerosoles Archive Stretch Boot
I have always had luck with Aerosoles. Their shoes are super comfy and durable, and you can wear them for 8 to 10 hours at a time. These boots got great reviews, and it's easy to see why: Classic, versatile, tasteful. Check the Aerosoles.com outlet section for even more fab deals.

Unlisted by Kenneth Cole Women's 'Saddle Up' Tall Riding Boots, $47.99 at overstock.com
For something with less heel and more edge, these riding boots from Kenneth Cole's more affordable line, Unlisted, will keep feet happy for hours. Again, Kenneth Cole is another brand I've had excellent luck with, so you can shop with some certainty that you will not be disappointed by your purchase.

Bandolino Neeko, $47.37 at 6pm.com
I've owned a couple pairs of Bandolinos over the years and they have never failed me. If tall boots aren't your thing, a low black ankle boot like the ones shown here are another fab option. You can wear them with dark bootcut jeans and a cute top and blazer for a stylish day to night look. Feet will be dry and pain-free, which means you will be a happy traveler.
Dear Readers: What are some versatile, comfortable shoes YOU would recommend that would work for winter in New York City?
Merrell Tibet Boot
Hunter Wellington
J Crew Nottingham
Did not find success in my gray suede flat boots, got wet so fast.
Hunter: http://www.thetannery.com/ProductDetails.aspx?g=3&dept=79&cat=84&subcat=461&pid=4412&sid=32651
Walked around Boston in these over Christmas and they are good for a few hours of shopping/ sights (works your calf a bit though). Excellent for traction in snow or rain which many fashion boots leave out and leaves you on your face.
Also found these cute and super comfy (order a little smaller though): Merrell Tibet boot - http://www.pagefootwear.co.uk/ekmps/shops/insmarc/images/merrell-boots-women-s-spirit-tibet-snow-boots-pigskin-leather-boot-200114-4980-p.jpg
For snazzy - J Crew boots are the best you can get for lower cost & comfort (check ebay or their clearance section on jcrew.com) they will not be the best for walking all day but for a few hours you are good to go: http://www.blogcdn.com/www.stylelist.com/media/2010/01/j-crew-nottingham-boot-240do010409.jpg (J Crew Nottingham Tall Boot) and they are great in a little bit of wet weather, even a bit of salt.
Best of luck!
They look so cute on the internet but I would warn buyers to find them in a store (my local DSW carried them in black, not brown) and see if they like them first. I found some gorgeous and comfortable riding boots with a similar build for just a little more money at the same DSW.