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An ankle boot creates a deliberate visual break that reads as intentional when the rest of the outfit is simple
A great many photographs of the period show these caps worn not only by newsboys, but by dockworkers, high steel workers, shipwrights, costermongers, farmers, beggars (such as Oliver Twist), bandits, artisans, and tradesmen of many types
The formal-attire dress code allows for a bit more flexibility with your tie choices and accessories
Straw hats were essential summer wear for outdoor activities like croquet
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