Squamates are ideal subjects for investigating relationships between diet and dental patterns because they exhibit wide dietary diversity, marked variation in dental shape, and are taxonomically abundant. Despite this, well-established links between diet and dental morphology are primarily qualitative in nature, with specific patterns of squamate dental complexity remaining largely unknown. Here, we use quantitative methods and a broad taxonomic dataset to quantify key patterns in squamate dental morphology, including re-examining the relationship between dentition and diet, testing for differences in complexity between dentigerous elements, and exploring the effect of ontogenetic dietary shifts in dental complexity in two iguanid genera. Our findings support previous research by demonstrating that species consuming more plant material possess more complex teeth. We did not find significant complexity differences between the left and right dentigerous elements nor the upper and lower jaws, with the exception of Amblyrhynchus cristatus, the marine iguana, which possesses significantly more complex dentary teeth than premaxillary and maxillary teeth. We find discordant patterns when testing for dental complexity changes through ontogeny. Amblyrhynchus, which is primarily herbivorous throughout its lifetime, increases dental complexity through ontogeny, whereas Ctenosaura, which is generally insectivorous as juveniles and herbivorous as adults, decreases dental complexity. Although preliminary, this research documents and quantifies novel patterns of squamate dental complexity and exhibits the possibilities for further research on the diversity of squamate dental morphology.