It’s always good to meet women who are not only beautiful, intelligent, and fashion savvy, but also happen to be pro at sports!  We had the opportunity to chat with DITTO founder Kate Endress about what it’s like to start a new company, transition from a career in investment to sports to fashion, and her perspective on the ever-evolving fashion and tech relationship:


What’s the most frustrating/difficult experience you’ve had while shopping online? 

I am a big online shopper, because I love the selection and convenience. Yet, I’m 6′ tall with a small head so I can’t trust that anything I buy online that is fitted – from jeans to glasses – will actually fit me. I am lazy when it comes to returning things so I really want to get it right the first time.  My goal with DITTO was to create the first online shopping destination that shows you how products actually fit you before you buy.

Given your background as an athlete and private equity investor, what was it that sparked your passion for finding the perfect pair of glasses? 

I am innately a problem solver.  In addition to the physical competition, I love the strategy of basketball.  I loved coming up with plays and moves that were surprising from back-door cuts to hook shots.  Similarly in private equity, I enjoyed helping companies fix problems, launch new products and grow.  I have always known that I would a start a company. After working for four years, I felt I had a good foundation and was ready to take the next step. I went to Stanford business school with the goal of starting a retail company that solved a real problem.  I spent the majority of my two years there working on DITTO. My initial idea was to do virtual fitting for everything from jeans to shoes to eyewear.  After interviewing hundreds of people and studied every vertical.  I realized that eyewear was the perfect place to start for several reasons:
1) People were really unhappy with the current process to buy glasses. From locked cases to confusing sizes, I saw a real problem with the current options.2) Eyewear has the lowest online penetration of any retail category at just 2.8% because fit really matters in this category.3) I am a big believer that glasses are the ultimate fashion accessory. The right pair totally changes your mood and your persona. Given it’s on your face, it is the often the first thing people see so it’s a very personal decision. Our technology can really help someone find the perfect pair. Not only can you try them on virtually but you can ask our personal (totally unbiased) stylists or your friends for personal recommendations.

How would you describe the ever evolving fashion + technology relationship, and how does DITTO’s concept help spark some of that evolution? 

Fashion and technology are fusing in exciting new ways.  In fact, there is so much activity, I’ve broken it down into four categories:

1) Information – Customers are also using an increasing number of online resources to connect and discover brands and products.  From streaming videos of the latest runway shows to pricing comparisons via QSR tags, there in no shortage of exciting content about the products we buy and the people who make them. DITTO is trying to facilitate this buy giving customers unique content about each designer sold on the site.

2) Ecommerce – The trend towards e-commerce is hard to ignore. Online spending was up 16% in 2011 according to Internet Retailer. Better selection, convenience and pricing advantages have me convinced this trend is no where near slowing down. Kudos go to UPS/Fedex for making the shipping fast and reliable (a big hurdle for e-commerce in developing countries). I think we’ll see free shipping & returns go further mainstream this year.

Virtual try-on technology (aka VTO) will continue to evolve. Webcams, camera phones and Kinect have made home-try on possible. Yet to date, most of the technologies have been focused on style – hovering flat images over each to give customers a sense of what the product will look like on them.  DITTO is at the forefront of this trend by creating the first of these technologies that actually show you if the products fit you – which is the largest hurdle to online shopping. We render the products in 3D so you can see how you look in the glasses from every angle.  We also scale the glasses accurately so you can see which ones actually fit.

3) Products – Technology is changing the products themselves. Designers are using 3D CAD systems to model clothing. Laser cutters are faster and cheaper than ever. 3D printers hold incredible promise to bring consumers truly customized products. And in our case, we use your DITTO to find a more accurate focal center for your prescription lenses and pre-adjust the end product (since no one really seems to have perfectly symmetrical ears).

4) Social – “Social shopping” is one of Silicon Valley’s favorite phrases, yet its usage varies widely. It describes everything from group discounts, marketplaces, crowd-sourcing, review systems, social media sharing, social media curation, and personal styling from friends.  Regardless of the nomenclature, one thing is true: people care about what their friends think, do and buy. DITTO lets you post a side-by-side of you wearing two different pairs of glasses so you can ask your friends “Which Look Best?” We let you share your DITTO with friends who can see your interactive DITTO and handpick your glasses.  I believe that this validation from people you care about will help give people the confidence to buy online.

Is a DITTO for trying on clothing on the horizon? 

The fundamental problem with online shopping is not knowing if the products will fit. This is definitely as true for fitted apparel as it is for glasses.  Any time there is a real problem, I think there an opportunity. Yet the worst thing a startup can do is spread themselves too thin.  We are focused on solving a real problem in the eyewear market – at least for now.

Written by Jacqueline Chambers

Jacqueline Chambers

Jacqueline Chambers is the founder of TGIFguide. She uses her innate skills as a natural “connector” to serve businesses, brands and individuals in the LA area and beyond.