This research examined the impact of usability guidelines and front-end web site design on consumer aesthetic evaluations of e-commerce web sites and perceptions of the e-retailer. A detailed web site design guidelines framework was developed from an in-depth review of the usability, human factors, and human-computer interaction web design guidelines literature. Four web site design factors (background color, white space, thumbnail image location, and thumbnail image size) were selected and varied using this framework. In addition, as a secondary research focus, this study explored the impact of these front-end web site design factors on consumer trust, product preference, and purchase intention. A conceptual model was proposed which integrated usability and web site design with consumer web site evaluation, trust, purchase intention, satisfaction, and loyalty. Conjoint analysis and optimal design methodologies were then used to design web page prototypes. Results indicated that subtle front-end web site design elements impacted consumer aesthetic evaluations of the web page and subsequent e-retailer evaluations. Results also provided support for the conceptual model developed.