Well I put it off long enough! To my surprise I had a really hard time with this. For all of the images I clipped to try, my limited closet lacked the one item that really made the look (e.g. slouchy trousers, hiking boots, long heavy knit scarf etc.). I kept coming back to this black look which was the one that immediately called to me (#1), but since my loafers have heels I feel it really changes the vibe of the look (#2).
I wanted an outfit I would wear all day but unfortunately it was freezing this morning (literally), and I just had to change into a version with socks (#3, what I am actually wearing today). To keep one brown element I added my cropped vest and swapped to socks+flats in spirit of menswear. I may give this another try when it's at least 50F :)
Comments, critiques, thoughts and questions welcome.