New technologies such as 3D simulation and digital prototyping offer endless design opportunities for gloves. One potential application is digitally draping, which can be used to improve glove fit. A pilot study with one subject was conducted to examine the feasibility of this approach applied to glove design and fit. The subject completed a fit survey and then had their hand 3D scanned. A glove was digitally draped on the subject’s hand scan in EFI Optitex®. The pressure map and mesh tool in Optitex were utilized to aid expert fit evaluations. The findings of this pilot study show that the 3D glove simulation can provide a robust understanding of fit. Designers can use this visual and quantifiable information as a way to improve glove fit during early design iterations, thereby potentially sparing resources. Additionally, better fitting gloves could potentially be an effective way at combating common hand injuries.