In 1994, heavy ice storms hit southwestern Virginia, causing extensive damage to trees. Larger trees tended to experience branch breakage while smaller trees were more commonly bent under the weight of the ice. Bent trees formed compression wood in the years following the ice storm. To evaluate the influence of tree size and location on the formation of compression wood, a commercial wood defect, 47 Pinus strobus L. trees were felled and cross-sections were collected at 0.5 m above the root collar. Disks were sanded and scanned, and the cross-sectional area of compression wood within each tree ring was quantified using image analysis software. In addition, wood anatomical features were quantified in the 3 years before and after the storm. Compression wood formation was significantly related to tree diameter and the 6–9 cm diameter class formed more compression wood area than any other size class (this class was 4–8 cm at the time of the storm). Trees > 18 cm at the time of the storm did not form any post-storm compression wood, suggesting a lack of stem bending at 0.5 m. Trees < 6 cm were able to right themselves with less compression wood formation than the 6–9 cm class. Post-storm compression wood contained significantly more cells per unit area than pre-storm normal wood, but no significant differences existed in cell wall area. Therefore, compression wood had a higher cell wall to lumen ratio, creating wood that is more structurally sound on the lower stem side. This research identifies which size classes of P. strobus are most vulnerable to post-ice storm compression wood formation, and sheds light on cellular characteristics that contribute to its ability to return gymnosperm trees to an upright position after displacement.