|John Hassall, 1907, Duke of York's Theatre lobby posters|
Artists who drew the boys immediately after the debut of the play in 1904 showed them as normal Edwardian boys in ordinary clothes. But the longer and more fully-realized version of the story in Barrie's book, published in 1911, takes pains to describe how the boys' garb differs from Peter Pan's suit of skeleton leaves and cobwebs.
They are forbidden by Peter to look in the least like him, and they wear the skins of the bears slain by themselves, in which they are so round and furry that when they fall they roll. They have therefore become very sure-footed.
Even shooting at the Wendy Bird, Flora White's 1914 Tootles looks adorable, even cherubic. This rather describes Tootles, actually, although artists have long seemed fond of thinking of the lost boys in general as sweeter than perhaps Barrie did.
The 1953 Disney animated film took the idea of the bear skins further and dressed the boys in full animal costume. The suits seem to take the place of differentiated personalities for these characters. And I'm sorry, but they're the ugliest lost boys I've seen. Plus there must have been some mighty big rabbits and foxes in Never Neverland.
Later artists such as Trina Shart Hyman (1980)
and Scott Gustafson (1991) were more faithful to the book's portrayal, with their lost boys looking roly-poly in their bear-skin coats.
The 2003 Universal/Columbia Pictures Peter Pan movie took more liberties with the boys' attire, but it makes sense that boys in a permanent game of make-believe would take creative advantage of whatever props they came across.
With the modern popularity of "dark" versions of children's stories came grimmer versions of the lost boys, portrayals which do not shy from the more murderous nature of these children. A good example is the group in ABC's Once Upon a Time. However, portrayals of the lost boys as teens, according to Barrie, are impossible. As he tells us, "...when they seem to be growing up, which is against the rules, Peter thins them out." (Dark interpretations of Peter Pan often miss the darkness that has been in the story from the beginning.)