Oral leukoplakias (OL) are potentially malignant lesions that are typically white in color. Smoking is considered a risk factor for developing OL, and dysplastic lesions are more prone to malignant transformation. The aim of this study was to describe the clinical features observed in dysplastic and non-dysplastic OL in both smokers and nonsmokers. A total of 315 cases of OL were retrieved and separated into either dysplastic or non-dysplastic lesions, and these cases were further categorized as originating in either smokers or non-smokers. Frequencies of the type of OL lesion, with respect to whether the patients smoked, were established. The results demonstrated that 131 cases of OL were dysplastic (74 smokers and 57 non-smokers), and 184 were non-dysplastic (96 smokers and 88 non-smokers). For OL cases in smokers for which information about alcohol consumption was also available (84 cases), the results revealed no significant difference in the amount of dysplastic and non-dysplastic lesions. Dysplastic lesions were more frequent in male smokers and in non-smoking females. The median age of smokers with cases of OL was significantly lower than in non-smokers; the lowest median ages were observed for female smokers with dysplastic OL. The most frequent anatomical sites of dysplastic lesions were the floor of the mouth in smokers and the tongue in non-smokers. Dysplastic lesions in smokers were significantly smaller than non-dysplastic lesions in non-smokers. Being a male smoker, being female, being younger, and having smaller lesions were associated with dysplastic features in OL. These clinical data may be important for predicting OL malignant transformation.