Hen's tracks and a crooked fence as similes for sloppy handwriting
When discussing his lack of literacy with Henry Fosdick, Dick likens his clumsy handwriting to “hen’s tracks,” or the clumsy scratches that chickens make with their feet, and also “a rail-fence on a bender.” By this he means that it is crooked, clumsy, and inconsistent.
Manliness as simile for fortitude
Dick says, somewhat sarcastically, that if some misfortune fell upon him such that he had to live on Fifth Avenue and be wealthy, he would “bear it like a man.” By that he means that he would stoically accept his fate without complaint.
Brotherly love as simile for rivalry
When Dick says Micky loves him “like a brother,” he’s speaking sarcastically because there’s actually a rivalry between the boys. Micky Maguire has just thrown a rock at Dick’s head. As with many of Dick's witticisms, this simile has a grain of truth: many brothers do in fact have a sibling rivalry.
Strange garret as simile for awkwardness
In church with the Greyson family for the first time, Dick feels “like a cat in a strange garret”: uncomfortable, out of place, and without any good idea what was expected of him. He feels awkward but resovles to keep up appearances despite his discomfort.
Astor as simile for wealth
Dick, exaggerating as was his habit, says that his tutor Henry Fosdick combines teaching with boot blacking, and will be “as rich as Astor” sometime, if he lives long enough. Astor was the name of an extremely wealthy industrialist who was famous for his money, his class, and his high standard of living.