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We see boys wearing peaked caps with a variety of outfits. It was a cap style commonly worn with suits. This was because it was so common to wear suits in the late-19th century. We see it being worn with different styles of suits, including styles not commonly associated with it. Younger boys might wear it with a Fauntleroy suit. An exception was the sailor suit, perhaps because their sailor headwear styles. Basically the peaked cap was worn with whatever suit style was popular at the time. It was a widely worn cap style at the turn-of-the 20th century. Gradually the peaked cap came to be seen as more of a upper-class style. We are not entirely sure of the mechanism at work here.
Upper-class boys were more likely to wear suits and attend private schools with uniforms. Some of these unifiorms were British styled with peaked caps.
We also note peaked cap that match the material and color of the suit. The peaked cap was especially common with the Eton suit worn by younger boys in America. Many American mothers considered it a necessary finishing touch for the Eton suit. Even after graduating to more mature style suits, however, a well dressed American boy from an affluent family might continued to wear a peaked cap until 12 or even 13 years old. These caps were especially common as part of any formal outfit. The peaked cap was especially common with short pants suits.
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