Eight people in costumey hats
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This little photo (about 3 x 4.25 inches) is amusingly mysterious to me. I dug it out of a bin of photos at a store. The bin had a couple others showing two or three of these same people in the same setting, but I was feeling frugal, so I only bought the one with everybody. And the others didn’t provide any more information or context than this one (and this one provides none). This looks like an ordinary photo of friends gathered for a group photo, until you notice the hats and neckerchiefs. It looks like the hats are an assortment of cowboy hats, sombreros, and Spanish hats (with the pom poms). And none of these people looks like they’d be wearing these hats on an ordinary outing. At the same time, it doesn’t seem like they are in full costume. And what is this setting? Are they gathered for a themed event? Are they salespeople outside their store modeling novelty hats? In any case, they seem to be having a good time.
Pics of Then 
Any of your guesses could be correct, but I’m thinking they could be an amateur performing group of some kind, because they’re all pretty close in age. The women could be a chorus and the man an MC. Do you think 1940s?
On second thought, maybe they aren’t all close in age. At least two of the women and the man look older than the others. But they could still be amateur performers.
That could be, too. Maybe a musical group or something.
The one in the boots has much more of an outfit than the others (note also the heavier skirt), so I’m imagining that either she was some sort of real cowgirl who visited this group (lecture for the garden club?), and the others put together some headgear to mark the occasion, or else she’s the only one who fully dressed up for office rodeo day!
Those are good ideas!