Understanding how similar design appears is a key element to understanding companies' design strategies. However, it is difficult to evaluate companies' design strategies with conventional style measurement methods since they only taxonomically measure whether a specific characteristic is included in a specific style. This study numerically measured car design similarities to synthesize and analyze car brand styles, thereupon discovering the design trends among car brands for strategic design positioning. This paper aims to find methods for quantifying style differences and identifying unique design elements of car designs among 23 automobile manufacturers based on design similarities of a large quantity of car designs (N = 119). To achieve this goal, a hybrid style quantification methodology a mixture of Fourier decomposition, eye tracker, and shape grammar was created to evaluate similarities, visual significance, and combinations of 19 car design elements. Fourier decomposition was incorporated to find the quantifiable values of design similarities of car design elements. Visual significance analysis was also conducted for each car design element through eye tracker to measure the importance of certain design elements for weighting factors. Then, each combination of design elements was compared with car design elements of other cars for similarity calculations. Finally, car design alternatives were synthesized, and transitions of design positioning were analyzed based on the similarity values weighed by the visual significance results. Using the suggested methods, alternate designs can be synthesized while preserving brands' design styles, and design trends can be analyzed for strategic evaluation.