Background: Chronic dermatophytosis is a considerable challenge in routine clinical practice. There is, however, scarce information available in the literature on its extent and characteristics. Aim: The aim of this study was to evaluate the host-related factors of chronic dermatophytosis and to identify the common fungal isolates. Methods: The study enrolled a total of 145 cases of chronic dermatophytosis attending the out-patient department of a tertiary care hospital in Jammu from November 2017 through October 2018. A detailed history was taken, followed by a clinical examination and investigations such as routine baseline investigations, an absolute eosinophil count, a wet mount for direct microscopy, and a fungal culture. Results: The most common presentation was tinea corporis with tinea cruris (33.1%), followed by tinea corporis alone. The majority of the patients (54.5%) had more than 20% of the body surface area involved. Most of the patients were manual workers (n = 44; 30.3%). The number of hours of sun exposure varied between 1 to 8.5 hours (mean ± SD: 3.53 ± 1.75 h). The fungal culture was positive in 65 (44.8%) patients. The most frequent isolates were Trichophyton mentagrophytes (53.8%), followed by Trichophyton rubrum (38.5%). Conclusion: We found Trichophyton mentagrophytes the predominant pathogen in chronic dermatophytosis, followed by Trichophyton rubrum, which demonstrates a changing trend as far as the causative organism is considered. Besides, various risk factors for chronicity such as prolonged sun exposure, lack of proper hygiene, wearing tight-fitting synthetic clothes, the use of topical steroids, and non-compliance to treatment were identified.