Nick Benson
5 min readJan 27, 2016

When we shop we are completing our vision of ourselves. That is to say when we adorn something that someone else will see we are contributing to our identity. With today’s hyper visibility of our identity we are acutely aware of how we represent ourselves through clothing, accessories, images, words and relationships. It’s an emotional thing. So… I shop therefore I am. This is actually true.

The things we acquire group together to form a projection of an identity. For those engaged in this pursuit, its a projection of the person they want to be — think tech workers wearing their company’s Tee Spring creation emblazoned with a logo OR a death metal loving fella wearing an old Megadeth tee. The things that we wear say a lot about us.

I was recently walking around the WeWork Labs Demo Day in New York and I came across a company whose goal is to help people find the dresses they’re looking for. Not easy. There is a very difficult problem of their being a lot of shit on the internet and us not knowing where or how to find it.

Finding something online is great if you know what you’re looking for and how to describe it. For instance ‘I want a Chinese Noodle restaurant in Chinatown in NYC’ is going to produce a number of relevant results BUT try searching for ‘I want to eat’ or ‘I’m hungry’... You might have a little more trouble. Algorithms don’t know what people want unless they tell them.

This company basically made a machine learning aggregator that helps you find a dress you ‘want’ by creating ALOT of data around a dress and it’s measurements, colour and other specifications and then showing you other products like it from other stores. Immediately I though of a user, wait… scrap that… I thought of how a person shops.

When we choose something to wear or when we shop, a big human factor is trust. We trust brands for their consistency in quality, value and design sensibility. These are decisions humans make. Ultimately we trust people. We trust stores for their relevant curation of products. We trust our friends for their opinion and taste. We trust publications for their ability to ‘cool hunt’ and tell stories that remind of us of who we want to be.

People don’t trust algorithms, people trust people. Think of our ‘Chinese noodles in Chinatown in NYC’. We get our results and where do we turn? Yelp or a reputable blog, some website with people’s opinions or we call a friend. Either way we trust people and hopefully we end up at Spicy Village.

We don’t trust in a garment’s specifications. If I’m buying a shirt does it come down to the measurements? Even if they could get granular enough for a guy like me, a guy who cares about what he wears and is very detail specific, is that meaningful enough for me to make a purchase? It isn’t. It’s important, but quality, brand story, company values, and craftsmanship also play a big role. I trust brands. I wear Tricker’s shoes, I love their quality, their attention to detail and their after market care. I wear APC jeans, I love their cut, the weight and treatment of the denim and the brand story of APC.

Ok so the app is for those that know what they want-ish.

I had an experience with Fancy, you guys remember Fancy right? I was early with the adoption of the app. I liked the idea and the interface but the recommendations… the recommendations were pretty good, maybe 90% accurate. The problem with 90% accurate is that I don’t want to be 90% of my idea of me. It showed me deck shoes. Eastland Made in Maine was the brand. I wear deck shoes. I buy a pair a year at the start of summer. I never buy Eastland Made in Maine, I buy Quoddy. Close but I don’t see myself as an Eastland & Maine guy. If you are going to attempt to know me, KNOW ME.

Quoddy Vs. Eastland Made in Maine. The difference is subtle… but it’s a difference that I identify with.

Trust is the ultimate commodity in online retail. I trust Mr. Porter. I know I will get products of a certain quality. I know I will get great aftermarket care. I trust their product descriptions. If I select a Drake's shirt I know the related items they offer me will be worthwhile. Now I think about the prospect of browsing products grouped together that are the same colour, length of sleeves or neck measurement and I’m less excited.

Human’s love stories. Measurements are data. Human’s don’t communicate in data points we tell stories. Great products tell stories. Online stores have been using content to sell products for a while now and it is EFFECTIVE. Mr. Porter journal is a powerful selling tool. Net-a-Porter’s Porter Magazine is a powerful selling tool. Content is king. Tell a story, sell a product. When you remove brand from the equation you are inhibiting an item’s ability to sell itself through narrative.

I believe that this company I saw can be successful in some way. There are ways to craft data into a shopping experience to make it richer. I think these guys need to ideate around how to integrate their powerful image recognition and machine learning tech with the way humans buy clothes. Sounds like an exciting challenge to me, and one that can have a great impact on the way we shop online.

Nick is the co-founder of design firm DREAM. We love thinking about things like this!

Nick Benson

A guy thinking about a bright future. Writing at the intersection of business & supply-chain… and sometimes what it means to be a person. • founder E xD Atelier