After the insertion of dental implants into living bone, the condition of the peri-implant bone changes with time. Implant-loading phenomena can induce bone remodeling in the form of the corticalization of the trabecular bone. The aim of this study was to see how bone index (BI) values behave in areas of bone loss (radiographically translucent non-trabecular areas) and to propose other indices specifically dedicated to detecting corticalization in living bone. Eight measures of corticalization in clinical standardized intraoral radiographs were studied: mean optical density, entropy, differential entropy, long-run emphasis moment, BI, corticalization index ver. 1 and ver. 2 (CI v.1, CI v.2) and corticalization factor (CF). The analysis was conducted on 40 cortical bone image samples, 40 cancellous bone samples and 40 soft tissue samples. It was found that each measure distinguishes corticalization significantly (p < 0.001), but only CI v.1 and CI v.2 do so selectively. CF or the inverse of BI can serve as a measure of peri-implant bone corticalization. However, better measures are CIs as they are dedicated to detecting this phenomenon and allowing clear clinical deduction.