Around the world and into the dressing room

An interview with Purva Gupta, the founder of Lily

Join us on Purva Gupta’s journey from an insecure teen with an acute stammer in India to becoming a woman with a chic sense of style in America who started Lily — a fashion app that uses machine learning to help women close the confidence gap through their clothes shopping experience.


Ariana: Is the confidence gap around clothing something you dealt with yourself?

Purva: As a teenager I suffered from an inferiority complex that led to acute stammering. I went from a small town in India to a big city and because I couldn’t talk in fluent English, I developed a stammer where I couldn’t even open my mouth. My parents took me to a doctor to find out why I wouldn’t talk. The doctor saw there was nothing physically wrong and that it was a mental barrier I had created. As I was graduating high school, I started conditioning my mind to feel beautiful, dressing well, and telling myself that I’m not less than others. Those things helped one day at a time.

Seeing how this changed me was playing in my mind as I was shopping in New York City. It seemed to me that the products were more important than the people buying the clothes. These were great brands and I’d walk out not able to find anything, frustrated, and think that there was something wrong with my body. I started questioning whether this thinking was true. I talked to over 1,200 women over three years, asking them what they bought, offline or online, and why they bought it. It boiled down to my realizing I wasn’t alone in this process.

Ariana: What you’re doing is using a ton of data on women’s perceptions and machine learning to address an emotional challenge for women when they’re getting shopping for clothes?

Purva: Correct, we start by focusing on the “why” rather than the “what.” The difference with Lily is that everyone else is focusing on browser history and purchase history and we’re focusing on what women are thinking as they’re shopping for clothes.

While the user is chatting with Lily, there is a body perception map on the back end. For every part of the body, there are different degrees of confidence that Lily has picked up on and that’s how the flow of the user’s experience is designed.

Ariana: Can you give me an example of ways you’ve seen how women think about themselves?

Purva: A friend of mine is 5’4” and she thinks she’s short. That’s her perception. The other perception that she has because she thinks she’s short is that maxi dresses will make her look short and stout. So, when she goes to a store and sees maxi dresses, she thinks that she doesn’t like them because they don’t look good on her. We want to understand such types of thinking as they’re interacting with Lily.

The key thing about Lily is that it’s breathing. It’s changing, reconstituting and learning with every single interaction of the user. It’s not like buying a box and getting a box of clothes every month and wondering if anyone is even paying attention.

Our service doesn’t just give lip service to feeling good about yourself, but gives you the tool to do that by giving you advice on clothes that flatter your body and change the narrative one recommendation at a time.

Ariana: These body perceptions start at a young age. Do you see Lily as addressing a larger issue than feeling confident when shopping?

Purva: The body perception starts for girls as young as two years old. They look in the mirror and start seeing body parts they dislike. Then they start comparing as teens, like, “My hands are fat compared to that of my friends.” Making these relative perceptions led to young adults with insecurities and feeling not good enough. Women in this country think 13 negative thoughts about their bodies every single day.

The problem isn’t how women look, it’s how they think they look. It’s all in perception. A recent study done by the UN and Dove Global that said that 8 of 10 girls are choosing not to do activities at school, pick up a game or a sport because they think they don’t look good enough. If half of the workforce in the world are putting themselves down because of a perception, what kind of damage is that doing to the world?

We try to understand the perception of the user and then based on that Lilly shows what flatters that user. When you feel negative about any part of your body, we’re trying to push it to the positive narrative. The is no right or wrong, but Lily will tell you with each item how it flatters you. We’re trying to help the user positively perceive their body parts.

NOTE: The results are speaking for themselves. Lily has been live for 11 weeks and already has more than 3,000 users who have bought more than $80,000 of clothes, and 1 in 3 users have bought on Lily. At SXSW this year in the award category of Social and Culture, Lily won Best Startup. On May 17th, they won Best Startup at the Startup Conference at Silicon Valley.