The word “best” in this title is, of course, subjective. What this gallery of a post features are some of my favorite boy with a hat paintings from the 18th to the 20th centuries.
Boys wearing hats are an interesting subject in painting. They wear on their faces the innocence of their young age, but mingled with it are other feelings or moods, not all of them straightforward.
The Torn Hat Painting Thomas Sully (1783-1872) Photo credit: Museum of Fine Arts Boston 
Portrait of a Boy in a Top Hat with Flies John Opie (1761–1807) Victoria and Albert Museum Photo credit: Victoria and Albert Museum, London 
A Peasant Boy with a Hatchet Painting Tropinin V.A. (c. 1810s) 
A Young Boy Seated in a Landscape Catherine Lusurier (c. 1753 – 1781) Photo credit: Sotheby’s 
Dutch Boy Painter Lawrence Carmichael Earle (c) 1906, by National Lead Co. 
Boy Fishing Painting by Eastman Johnson (1860s) Photo credit: Cleveland Museum of Art 
Boy with a Hat Painting by Michiel Sweerts (circa 1655) 
Portrait of an Unknown Young Boy in a Hat Carel Fabritius (1622–1654) Photo credit: National Trust Images 
Portrait of a Young Boy by Ludwig Knaus (1829 – 1910) 
Portrait of Camille Roulin 1888 Vincent van Gogh
Not all of these paintings are what you would call cute: take the boy with a hatchet, for example.
To some extent, these paintings chart hat styles through the ages. Not two of the hats are quite alike, are they?
Let’s not forget that not so long ago, hats were about as ubiquitous as sports caps are today, and decidedly more stylish…
What do you make of these paintings? Is there any one in particular you like?
boy with a hat 
I like the boy fishing.
I like that one too! Though I can’t decide whether it’s summery or autumnal, not just because of the hues, but because of the pants!
All gorgeous, but my favourite is the Catherine Lusurier painting.
I love all these paintings. It is difficult to choose one hat. I might go for Catherine Lusurier’s one.
The torn hat is undoubtedly my favorite. Mostly because my grandmother recreated this piece in an early art lesson and I grew up seeing it… while it was different from the classic, the essence was there. The unexpected light in what should be a dark shadow of his face makes it interesting to me and he has an adventurous spirit. I can tell