Always love your WIW's and these are no different. The first one (of you) is my favourite.
Short pants and shrunken suits are big in The Big City, especially in the downtown banking and insurance sector where I work. Groomed hair (short sides, longer top, fade in back) and tidy beards are big. Not so much hipster as 'metro sexual'. I think the shrunken suit/short pant works better on a shorter man with a trim build. Older gents dress more conservatively, but coordinating shirts, ties, and socks is popular. Regardless, I enjoy a well dressed man and the colour is fun!
My menfolk, like Janet's DH, are tall - all over 6ft 3in with troublesomely long inseams. Despite their age ranges - two 20 somethings, and a 60 year old - they can't seem to get over the scars left by taunts over 'flood' pants - so no fashionable rolled cuffs or shrunken suits here!