Although street vendors are contributing a lot to our society and economy, they have to face several difficulties every day in order to sustain in this trade. The study was conducted to find out the major problems they face while operating their business. A total number of 105 street garments vendors were selected from different parts of Dhaka City. A questionnaire, having reliability score over 0.7, comprising both close and open-ended questions were filled through scheduling method. SPSS 22.0 has been used to analyze the data. The study explores a positive correlation among the respondents’ investments, earnings, and monthly savings. Factor analysis was conducted and four factors, having cumulative factor loading over 50.493% and eigenvalues over 1.0, were retained to group (through rotated component matrix) all the items under study and these are labeled as market and financial difficulties; political, legal, and administrative difficulties; organizing and managerial difficulties; and health, hygiene, and environmental difficulties. The study concludes with some recommendations so that the street garments vendors can enjoy secured business life along with proper recognition and harassment-free business opportunities.