It was a breezy evening while taking these pictures, hence the title of the post. I also felt that the look fit the bill as well since there's nothing more casual and comfortable than a loose button up top and your most worn pair of jeans. The ankle wrap heels are a new favorite since ankle wraps are everywhere right now. See: Isabel Marant, Aquazurra (here, here, here and here) Stuart Weitzman, Manolo Blahnik etc.
Ever since I saw the video of Leandra Medine from The Man Repeller interviewing Jenna Lyons, President and Creative Director of J. Crew, I only roll my sleeves the way the Jenna shows. If Jenna shows you the right way to do something, you do it. Fast forward to 1:00 to see her show us how to roll.