Designers faced with the task of developing a new product model of a brand must balance several considerations. The design must be novel and express attributes important to the customers, while also recognizable as a representative of the brand. This balancing is left to the intuition of the designers, who must anticipate how customers will perceive the new design. Oftentimes, the design freedom used to meet a product attribute can compromise the recognition of the product as a member of the brand. In this paper, an experiment is conducted for measuring changes in ten styling attributes common to both design freedom and brand recognition for automotive designs from four brands, Audi, BMW, Cadillac, and Lexus, using customer responses to two- and three-dimensional vehicle designs created and presented interactively through a crowdsourced web application. Results show that while brand recognition is highly dependent on the manufacturer, two brands have strong negative relationship between design freedom and brand recognition, suggesting that these two manufacturers face a significant challenge when evolving their respective brand styling. This study is a first effort toward quantifying and predicting tradeoffs between design freedom and brand recognition, contributing to existing efforts that augment human intuition during strategic design decisions.