late 40s possibly but more likely early 50s I have a different pair of a similar design. 40s would be a little sharper around the instep. Thats spadey bit on the last and the two tone sole is very 40s.
7.5E fitting 1920/early 30s in remarkable shape. Heels are a deadset give away with the 8 holes. Normally that heel would be hard and shriveled. These obviously stayed in a box in a ventilated area.
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