Industry Interview: Jennifer Simons


We sat down with Jennifer Simons, the Founder & CEO of Dressmate to chat about her innovative community-based rental company, where she hopes to take Dressmate, and pitching for capital as a young entrepreneur.

Can you start by giving a brief overview of your background?

Sure! I recently graduated from Georgetown University. I started out in pre-med and math with the hopes of becoming a doctor, but after I started Dressmate in my sophomore year, I switched gears and majored in Theology. My mom, who is a Korean immigrant is still hoping I’ll magically become a doctor- but she’s super supportive of Dressmate!

That’s amazing, good for you! And for our readers that don’t know about Dressmate, can you explain it?

Dressmade is a peer-to-peer clothing rental marketplace that’s currently exclusively available on college campuses. We are made by women, for women. Ultimately, we are on a mission to make the world more sustainable and bring like-minded woman in various communities together.

What prompted you to start Dressmate?

I got the idea when I saw the need through my own experiences. Back in college, I bought a dress for an event and it was quite stressful. College shipping is a nightmare because everyone purchases things online so it takes a while and I was never sure if clothing items would arrive on time. Unsurprisingly my dress didn't come in time, and I thought about other times when clothing accessibility was a problem. My freshman year roommate was on full scholarship and would borrow clothes from me on occasion - even that didn't make sense. She is 5'3" and I am 5'10", but the lack of an easily accessible platform meant that I was her only option. From those experiences, it promoted me to start Dressmate.

What did the early days of Dressmate look like? Did you have a website right off the bat?

No, it originally started as a Facebook group and Venmo account. I posted photo albums with the clothes and skipped classes to do transactions. It took a while to pick up and I honestly wasn’t sure if it was going to work. However at Georgetown, we have this annual event called the Diplomatic Ball, and it’s basically like prom. Girls rent nice dresses from companies like Rent the Runway, Poshmark, etc. From Dip Ball, we got a number of transactions and it’s taken off ever since.

That’s amazing! And who would you consider as Dressmate’s target market?

We are only at US college campuses right now, with the exception of one experiment at Glossier’s New York office. Our main target is females aged 18 - 22 years old, but if the campus has grad students, the age can be skewed higher. So far we haven’t had a lot of male interest but if men sign up, we are happy to accommodate!


Can you tell us more about Glossier’s NY beta test?

When I decided to do an internship, I had my mind set on Glossier. I love Glossier - I feel like the brand’s community and vibes are what I want to embody for Dressmate. When I was interning at the New York office, the interns often went for coffee and talked about what was going on in everyone’s lives. When I told people about Dressmate, it wasn’t my intention to do a beta test at the Glossier office, but it worked out that way. A lot of people at the office wanted to try running Dressmate at Glossier, so we did that. From that experience, I realized that offices are no different from college campuses and really, we just need a central location where everyone goes and is available to swap their clothing items.


That makes sense and it’s so cool you were able to try it out at Glossier! Where do you want to take Dressmate in the next year - are you planning to open in more offices?

Our immediate goal is to focus on expanding to more campuses in the US - we are targeting to hit 100 schools! After that, we want to extend how long we keep our customers by opening options for renting in other communities or companies.

Are you also passionate about sustainable fashion?

Yes, definitely! Once I learned more about the harmful effects of fast fashion, I stopped shopping at traditional retailers for a year and only bought second hand from Depop, Poshmark, etc. I really started minimizing my life as well. Originally I didn’t think a lot of people would relate to slow fashion and thought Dressmate’s value proposition was getting great clothes at a cheaper rate, without having to buy new items for each occasion. However when we did a survey, there was a general desire to be more sustainable and this issue was important among my target market. In general we found that people are resonating with brands like Everlane or Reformation.

From an investor perspective though, they understand the need for social capital, but are also concerned with how it affects the bottom line. However, it’s my personal mission that people understand and relate to the slow fashion lifestyle.

Speaking of investors, how has pitching gone? Have you seen any difficulties as a young, female entrepreneur?

I find that it really depends on the investor. For instance, some women don’t relate or get what we’re doing with Dressmate because of their socioeconomic background. For example, if a venture capitalist was an ex-investment banker, the woman could afford spending money on new clothes so she might not understand why someone would spend the time and effort to rent out a shirt for $15. Therefore, it can be hard when the woman doesn’t resonate with the target market, or never was the target market. When it comes to men, it can be a bit easier. They admit to not understanding the market as in-depth as we do, and trust that we get it.

I think our biggest battle right now is differentiating ourselves from other companies that came before us. A lot of money went into similar rental companies in the past 5 - 10 years and not much has come of it, meaning a lot of that money was lost. Because of that, some people are hesitant to invest in our model. However, Dressmate is different because it’s about community based rentals and we can’t be grouped in with Rent the Runway, or Poshmark. This means we spend a lot of time educating on our differences.


That’s great! I’m curious, what does an average day or average week look like for you?

I wake up early to attend to emails, submissions, and organize myself for the day. I enjoy listening to a podcast in the morning to keep me motivated and provides structure to my routine. Then, I’m off to a bunch of meetings that consist of conversations with other founders, investors, potential employees, etc. I’m currently in an incubator program, so I’m encouraged to meet as many people as possible. I get home at around 9:00pm to eat a late dinner, hangout with my boyfriend and cat, and typically watch an episode of TV. After that, I go to bed. Ultimately I try to balance friends and the business, but it can be hard sometimes. Entrepreneurship is not always glamorous!

How did you balance all of this in college?

It was difficult. At times, I felt like there was no balance. When I started working on Dressmate, I prioritized it over everything. Pre-Dressmate, I was a straight A student and on track to becoming a doctor. Once I started Dressmate, I started realizing that there were things other than getting a good grade and success is not black and white. Ultimately I made time for my business, but still studied topics in school that I was passionate about.

To close things off, what does success mean to you now?

Success to me means creating a strong, educated user base through Dressmate. I want to have a community of women that really understand what we’re doing and relate to our brand. We’re trying to build a group that understands the effects of fast fashion and reject it. Ultimately, we want to take things back to the older norm of buying fewer things that would last longer and help everyone get the most of their closets and clothing pieces.

thank you for taking the time to answer our questions Jennifer! It was a pleasure chatting with you.

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