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Dating my vintage bicycle

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That looks like a 1930s-era bike to me. KB-7 is the model K transmission, with drum brake, made in 1937. I would say late 1930s. I wonder if the fenders might be replacements, given the apparent difference in condition. But a careful examination and disassembly for cleaning may show more about whether those are original.
I think @SirMike1983 may be correct re those mudguards.
I've checked through the UK catalogues and the peaked mudguards are definitely a 1949 and onwards feature, with or without the chrome trim.
Catalogues from 1930 to 1948 show plain/flat mudguards.
The 1949 catalogue has the peaked mudguards featuring for the first time.

The chainguard on your example may also be an anomaly. From 1930 to the mid 50's this style of chainguard is only shown on ladies models.
Gents models, particularly 3-speed versions, always had full chainguards covering the top and bottom runs of the chain. Singlespeed models are always shown with no chainguards whatsoever.
Perhaps your chainguard was installed at the same time as the mudguards.

The badge changed design in 1950, so your example pre-dates that.

The 1930 catalogue features BSA X-pattern style chainrings; your design is featured in the 1935 and 1937 catalogues, and by 1939 the chainring features the 'Hercules' wording.

The only model I could find with cable operated drum brakes features in the 1937 catalogue.
It's not featured in the 1935 or 1939 catalogues.....
1453530


...looks a likely bet to me, with the obviously different mudguards/chainguard as previously mentioned.

Sorry I can't help further, and this may all be irrelevant as they may have done things completely differently for the USA export market.

Just keep riding it!
 
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