Spend $25 on an REI membership, you will be glad you did. I've almost exclusively used their own gear or gear I bought from them to live outdoors in Alaska all summer, experiencing all four seasons from May-August, and it never let me down.
A lot of those cold winter boots are really not comfortable and often don't last very long, as well as being kind of fugly. All that extraneous fur and fluff is just something else that can get wet and dirty. If one isn't dealing with sub-arctic temps the best boots I've found are Keens, stylish and practical, and come in half sizes, unlike almost every other boot out there. Don't forget socks, Smartwool is great as is the REI house brand.
I adore these
http://www.keenfootwear.com/us/en/pr...silverton%20wp and though the retail cost is a bit high I've found their items on sale at REI and Sierra Trading Post. I don't think you can easily get them outside Canada and the Lower 48, but the best boots of all time are Lobbens from Norway. If you're interested
www.piasweaters.com in Anchorage sells and ships them with no Alaska state tax. I only had to buy a new pair because I had foot surgery and my foot became narrower and longer, and I rocked that pair for over a decade. They are also lighter than regular boots and the traction is great, I know people in the mushing community who swear by them. I keep a pair of flats in my office or carry in my bag to change into so I don't overheat while I'm inside.
As far as coats go, many Columbia coats are excellent, I have a waist/hip length one with a zip out fleece I often wear. Depending on the weather and the streets I'll pair it with a light pair of snow or rain pants to keep dry and clean between point A & B. The pants I have from REI (Ultra Light Pants & matching jacket) have survived multiple archaeology digs and pack down into their own bag so I can take them off and look presentable while not carrying around wet outerwear. However if there is a melt issue and splashing, I wear a longer LL Bean raincoat with a removable wool/down lining that comes to my knees and keeps me dry all over. It went up in price but it is good for more than one season since the lining zips in and out.
http://www.llbean.com/llb/shop/65931...9-ppodxs&dds=y
Other than my boots everything I own is a bright color so I can be seen on dark or gray winter days and it does add a bit of cheerfulness. I have worn thinner Isotoner style gloves with the special finger material to use on my smart phone and iPod inside a pair of mittens. I knit my own mittens and hats, and the last commercial pair I owned my mother got me from Iceland and they just need thumb repair. I don't often need thermal underwear unless it gets to 0, but I found Jockey brand at Ross that is the thinnest, most durable, and outrageously comfortable I've ever owned.