With the invention of photography we know much more, but of course this means that we have headwear informationn for a relatively narrow range of the time that boys wore dresses, only about five to six decades. Early photographic formats show boys wearing dresses, but headwear with those early images are still rare (1840s-50). Even so we have found a few images with headwear. One early tin-type we have found shows a younger boy wearing a plaid dress with a rather decorated wide-brimmed hat. The Dags which first appeared in the 1840s are rather difficult to date. Ambros are relatively easy to date because they were done in such a narrow time frame. Tin-types are more difficult, but the cased tin-types generally date to the 1850s. And they were done in coniderable numners, nothing like CDVs, but far greater than the number of paintings in the earlier periods. Decorated hats are something we do not see later in the century, even very young boys. Unfortunately we do not have enough images from the 1850s to assess trends during the 1850s in any detail.
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