Cute! And definitely shows a bit o' wind in the area. In fact his hair is so windblown, you can't tell what the leash attaches to! From a technical standpoint, you may want to apply a bit (or a bit more) sharpening and level the shot so the curb is horizontal.
It's actually not a very good photo. However, I feel it meets the challenge better then most photos. I wish it would do better then the ones that pretend to show the effects of wind. I'm sorry, but birds flying is not 'Wind' - your photo is.
So that's what a widget looks like? :D Certainly is windy enough - you've got that covered. A couple of things might be holding this down some; 1) it's a little blurry - not quite sharp and well focused enough, 2) needs a little more contrast - as is, it's coming across somewhat flat. Good luck in the challenge.
The image appears out of focus on my screen - even the gray decking seems a little fuzzy. I would have recommended turning the dog around and having it face into the wind and see the expression on its face.
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