An old lady and a young man pass each other in the street, wearing exactly the same pale blue, beige and dark blue checked coat. The old lady is pointing to the young man and grinning.
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Hipster affirmation
I think that's what bothers me. From the picture, you can tell the lady is wearing an outfit. The gloves, the hat, the boots, the scarf; they are all pulled together. From the back, it looks like the guy's coat is not as striking and coordinated. Maybe it's just the orange/cream shoes, blue socks, and khaki pants rolled up, maybe it's because the picture is from the back, but it looks like he's wearing a bathrobe while she's wearing a coat.
The points you made about his outfit were all things I noticed as a mark of style. Basically I took those indicators as a sign that he can indeed pull off wearing this coat.
I think the lady was targeted for a prank. They may know the lady likes to wear the coat and bought exactly the same one then arranged for them to meet on the street.