The present research paper is focused on understanding the purchasing practices of male to female transgenders living in Chandigarh. It also studies the perspective retailers of apparel stores have towards transgender customer. Keeping this in view two sets of questionnaires were prepared to collect data. One focused on responses from male to female transgenders and second focused to collect reaction of retailers of apparel stores towards their transgender customers. 31 transgender respondents and 30 retailers of apparel stores were approached to fill the questionnaires. Sample of retail store respondents was further divided into two; 15 respondents from market place of Manimajra Chandigarh and 15 respondents from Sashtri Market, Sector 22 Chandigarh were taken. These markets were selected on the basis of the response of transgenders regarding the places where they liked to shop for apparel. The responses showed that the transgender community is becoming comfortable in the society. They do not feel threatened by people around them. 25.80% of the transgenders are of the opinion that the society is friendly towards them. They reported that social media had a role to play in their social acceptance and also help 67.74% of them to gain knowledge about the fashion trends as they feel interested. Majority of the transgenders like their garments to have a personal touch and therefore 54.83% of them design and get them tailored. On being asked about their wanting exclusive apparel store for transgenders, mixed reactions were received. 42% strongly agreed with the idea and 32% strongly disagreed. Comfort and fitting of garments were observed to be the two main factors affecting the apparel buying decision of transgender customers with 45.16% and 41.93% respectively. 74.18% of the transgender respondents found shopping to be stress relieving and fun. It was also seen that like male and female genders, 35% transgenders also end up spending more than their planned budget, showing that exhibiting impulsive buying behaviour was human nature. 55% retail store respondents treated their walk-in transgender customers like any other customer visiting their shops. 30% of the transgender customers visited their stores to buy party wear and 32% casual wear clothing. The store respondents never faced any difficulty in attending other customers in presence of transgender customers. They did not exhibit awkward behaviour and did not embarrass the store attendant asking for discounts.