Background: Psychological stress affects the normal hormonal balance in women hence causing irregular behaviours such as menstrual irregularities. The hormone cortisol is raised due to chronic stress hence reducing the level of female hormones such as estrogen and progesterone, thus the menstrual cycle. Aim: This paper aimed at establishing the association between psychological stress and hormonal changes with irregular menstrual patterns in women. Methodology: A cross-sectional survey design was used in which 200 women aged 18–40 years with irregular menstrual cycles were followed. Self-reported stress was measured in terms of perceived stress each month using the Perceived Stress Scale while hormonal samples of cortisol, estrogen, and progesterone were tested. Participant diaries held information on menstrual cycles, and mixed-effects regression by comparing stress, hormones, and irregular cycling patterns were used for analysis. Results: Higher PSS was related to the increase of cortisol levels (β = 0.45, p <|0001), and higher cortisol levels were linked to the decrease of estrogen (β = -0.9, p < 0.01) and progesterone (β = -0.4, p < 0.01). The effects on cycle length and ovulatory rates were greatest during the two months with the highest cortisol levels (month 7 and 8). Recovery of hormonal values was recorded as stress levels reduced, pointing to the possibility of the effects or stress on reproduction to be reversible. Conclusion: The study points towards psychological stress as being central in hormonal imbalance and menstrual disruption. Thus, this work underscores the need for multiple component stress interventions in gynecology to enhance reproductive health. Thus, future studies related to the current topic should be conducted to establish a connection between chronic stress, the durability of its consequences, and the effectiveness of interventions.