Jack Sparrow he is not but a heady imagination always takes you to places of wondrous adventure. This ad is from 1920 when the world of high fashion was transitioning into a more modern appeal. His outfit actually would have been at home from 1900 onwards and boys wore short pants until they attained the age of manhood and could don their first pair of long pants.
Cream of Wheat has been around since 1893 and is most represented in this era by their personification of the African-American cook "Rastus", a line of ads that is looked at as being racially disparaging today. This is actually the first ad I have come across from this company that did not involve Rastus in some form or another.
Cream of Wheat is of course still made today and is surprisingly still owned by the same company, not having been snatched up by one of the cereal conglomerates over the years. I haven't had cream of wheat in years, it was never a favorite of mine as I prefer to eat oatmeal as my hot cereal in the morning.