Bridge designs are studied through the lens of the three measures of structural art. The three measures, introduced by the Scottish engineer Thomas Telford in the 19th century and further developed by Princeton Professor David Billington, are the scientific, social, and symbolic aspects of the structure, referring to structural efficiency, economy, and elegance, respectively. Structural art is achieved through an elegant, still cost-effective structure, which displays its function clearly with its form. A case study using Streicker Bridge on Princeton University Campus is presented. The structural system is shown to be efficient and then the structural behavior is verified using Structural Health Monitoring based on fiber optic strain sensors and a Finite Element Model. A cost-comparison with similar bridges is used to assess the cost-effectiveness of the bridge, with emphasis on the life-cycle cost. The elegance of the bridge is evaluated through the choice of form for structural purposes and the bridge interaction with the users and its surroundings. The discussion shows that new technology and approaches are applicable to the concept of structural art and they are demonstrated using Streicker Bridge as a case study.