Multiple measures of vowel overlap have been proposed that use F1, F2, and duration to calculate the degree of overlap between vowel categories. The present study assesses four of these measures: the spectral overlap assessment metric [SOAM; Wassink (2006). J. Acoust. Soc. Am. 119(4), 2334-2350], the a posteriori probability (APP)-based metric [Morrison (2008). J. Acoust. Soc. Am. 123(1), 37-40], the vowel overlap analysis with convex hulls method [VOACH; Haynes and Taylor, (2014). J. Acoust. Soc. Am. 136(2), 883-891], and the Pillai score as first used for vowel overlap by Hay, Warren, and Drager [(2006). J. Phonetics 34(4), 458-484]. Summaries of the measures are presented, and theoretical critiques of them are performed, concluding that the APP-based metric and Pillai score are theoretically preferable to SOAM and VOACH. The measures are empirically assessed using accuracy and precision criteria with Monte Carlo simulations. The Pillai score demonstrates the best overall performance in these tests. The potential applications of vowel overlap measures to research scenarios are discussed, including comparisons of vowel productions between different social groups, as well as acoustic investigations into vowel formant trajectories.