That said, the Pillow boots are far more of a full-on winter option and not so much a transitional weather type of boot. They seem perfectly built for trekking through snow, slush and the dreaded cold, not to mention their less bulky sensibility in comparison to most winter footwear options would seduce any city slicker who wants something a little different than the token Sorel/LL Bean alternative. Not to mention how crazy comfy they are. I've gotten to know the Cougar brand over the years and their schtick is highly compelling - great boots, great prices and great history. They pretty much have a model to fit every lifestyle, so i would highly recommend to check out their website (CougarBoots.com) to see what they got going on.
One last thing - it would be awesome if you guys could fill out this survey. Not only would it help Cougar better cater to their market (you guys!!!), but for each one filled out they will donate 2$ to the Red Cross.
Leather jacket - Vintage
Plaid button down - Vintage
Cords - Rag & Bone (get a similar style here)