Sarah, wow, thanks for the tip on the insoles! I had no idea they made such a product. Sounds great, especially since I don't like to wear very thick socks.

As for a button-down shirt: I do have a few nice-fitting ones, but I always have trouble placing the collar. Should it be inside the jacket? Outside? Do I leave some buttons opened? Do I close it all the way up? If I leave buttons open, the collar always moves and looks misplaced... Or maybe the shirts actually don't fit me well after all and that's why I can't fit the collar into the jacket?

I will post some photos later... I would love to have this issue figured out. (This is how I found this forum a couple of months ago--searching for tips on where to place the collar! There was a good post from Angie but still I couldn't make my shirts work.)

My daughter just got a pair of alpaca (felted) insoles and she loves them. Especially since she got them at the farmers market from t hefarmer who raised the alpaca... They are both warm (insulating a pair of boots that isn't properly winterworthy otherwise) and very cushioning.

I agree with what everyone else has said (I did on-campus interviewing in freezing cold several years ago). Your JCrew suit and Express pants look great. I generally aimed for a mismatched suit look (i.e., black suit pants with a grey jacket on day 1, grey pants with a black jacket on day 2). I used a wool turtleneck in a strong color or a bright silk shirt under the jacket, depending on the weather (I think my collar was inside the jacket collar but I am not sure ).

Sheepskin insoles are a great idea (I bought Ugg insoles on Zappos last year). I use black booties as my main "interview/presentation" footwear in winter (mine are Clarks Dara III, which are weatherproof, whatever that means). I like wearing them with knee-high warm socks (much higher than the top of the booties), otherwise my socks gradually slide down, and the booties end up rubbing the skin raw.

I bought this tote recently for travel http://www.zappos.com/michael-.....south-tote (on sale at Nordstrom), and I think it might also work as laptop/document carrier.