This is an upland species of oak tree. The leaves have 7-16 pairs of rounded teeth. It is named for its resemblance to the unrelated American chestnut leaf. This distinguishes it from the somewhat similar swamp oak (Quercus bicolor) that has 4-6 pairs of teeth per leaf.

There has been a lot of confusion of the chestnut oak and the swamp chestnut oak (Quercus michauxii) and some botanists consider them the same species. The leaves of the chestnut oak are usually somewhat leathery and may be slightly hairy beneath. The twigs are hairless and end buds narrow and sharp, mostly over 3/16 inches long. The trunk of the tree is dark and deeply ridged, a trait used to distinguish it from similar species. The chestnut oak grows 60 to 70 feet tall on average and has a trunk diameter of 3-4 feet.  The fall coloration is red, much like that of the red oak, white oak and pin oak. It is sometimes called the rock oak.