Dressing up to go to the tailors to order a tailor-made suit ... that's when you know you have arrived. Note the tasseled cushion Bob is sitting on. It's not your basic Target shopping experience ...
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I'm guessing it's 1929, early 1930 at the latest. It's the hair, all wavy/curly, not slicked back at all. Just gorgeous, as is the young Mr. Montgomery is in his entirety.
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