Jewelry identification and evaluation are limited owing to interference from the surrounding metal mount and adjacent gemstones. To maintain transparency in the jewelry market, this study proposes imaging-assisted Raman and photoluminescence spectroscopy for jewelry measurement. The system can automatically measure multiple gemstones on a jewelry piece sequentially, using the image as a reference for alignment. The experimental prototype demonstrates the capability of noninvasive measurement for separating natural diamonds from their laboratory-grown counterparts and diamond simulants. Furthermore, the image can be used for gemstone color evaluation and weight estimation.