I have been researching the subject of boys who, during the late 1800's wore dresses and how long they actually did wear them durnig their childhood. I have learned that boys wore dresses as long as their 11th birthday. I continue to be interested in this because of personal reasons. I have always wondered about this but also I am of Scottish ancestory and they have worn kilts for as long as recorded history. The two paragraphs below represent exerpts from the Historical Boy's Clothing webpage with main contributions from Mr. Christopher Wagner. You can visit their webpage by clicking on the HTML link at the bottom.
Why Boys Wore Dresses- Most modern readers find it strange that boys used to wear dresses. Many modern observers describe the practice as dressing boy like girls in a tone of disapproval. Actually boys were not being dressed as girls. In fact, dresses were considered to be children's wear not specifically girls' wear. There are many reasons why this practice developed. Actually it is a common practice in human society to distinguish boys from young men, often by clothing or in primitive societies body adornment. (Notably it is not nearly as common to distinguish girls from young women.) Often elaborate ceremonies accompany coming of age celebrations. There were also practical reasons for outfitting boys in dresses. One very practical reason was it was easier to care for a young child in a dress who was not yet toilet trained. Other social issues were involved. The care of young children was considered to be the almost exclusive concern of the mother who generally felt dresses were more attractive outfits for boys than trousers. * Taken from Christopher Wagner's introduction to Boy's Clothing.
Breeching Age- The proper age for breeching a boy was a matter of heated debate throughout the late 18th and 19th century. There was no set age for wearing dresses. It was basically at the digression of the mother. As a result, there was a wide range of age for boys wearing dresses. For the most part, almost all boys wore dresses when they were 1-3 years old. At about 4 years of age you begin seeing boys wearing tunics, pants, kneepants, and knickers and the other more boyish outfits of the day. Until the late 18th century this mean scaled down versions of their fathers' clothes. Beginning in the late-18th Century and early-19th Century specialized clothing for children appeared. Most boys by the age of 5 or 6 years began wearing boys' clothes. Some doting mothers, however, did not want to lose their little treasures so early. So boys were not infrequently kept in dresses for several more years.
Such boys might wear dresses until 7 or 8 years old and some boys as old as 11 years are known to have been kept in dresses--although this was relatively unusual. There was considerable discussion during the late 18th and 19th Centuries. Earlier such discussion were primarily held within the family. By the early 19th Century, however, an increasing number of magazines were being published offering advise to mothers on child raising. One of the issues addressed was breeching. It was not unusual for "experts" to claim that breeching shouldn't be done before the age of 8 years. Most commonly the experts advised that the age had little to do with breeching--much more important was the child's size. Though the precise age was mostly left to the mothers digression, the general consensus was that breeching should take place before it was too late. "Her disposition, with her natural feminine tastes and tenderness, is always inclining her to deck her child with the gewgaws of finery and coddle him with the delicate appliances of luxury," one 19th Century book advised mothers. The expert continued, "The timely check from the manly boy may therefore prevent her from persisting in an effeminating process which would be sure, if continued, to deprive him of his best characteristics." [Bazaar Book of the Household, p. 214] Christopher Wagner (Historical Clothes of Boys)
Pictures don't lie as I have learned here. In my research, the overlying fact that remains is that boys suffered no pschyological confusion over this childhood of wearing the same clothes as their sisters did. Articles read on the webpage from men who were shown in the photographs having worn dresses said they never felt they were wearing anything that was wrong. The mother was always the one person who decided what their child wore and noone had any problems with that. So why should it be wrong today ?