Interview with StyleSeek Creative Director Ryan Plett

StyleSeek is a platform incorporating the three burgeoning trends of menswear, social media and personalization. Providing a customized experience by filtering products, style-specific links and labels to fit every user’s own style, StyleSeek offers a unique, easy-to-use processing tool for the average guy wishing to dress better. Helmed by Creative Director Ryan Plett, of [you_have_broken_the_internet] fame, the site is part of an exciting evolution in men’s online retail. We recently had a chance to sit down with the Chicago-based entrepreuner, photographer and menswear personality to delve into the conception of StyleSeek, his personal style, and the fashion start-up scene.

Can you introduce yourself?
My name is Ryan Plett; I grew up in Iowa, went to college in Minnesota, and have been working in Chicago for the last decade. In the “menswear” world, you might know me from [you_have_broken_the_internet] and TravelWell.

What’s your background?
Starting in college, I worked for a large retail clothing chain, doing everything from folding shirts to designing in-store marketing, and then opening new stores. After that I went into the sports performance industry to work in marketing and design input for running shoes. Unfortunately, what I thought was my dream job was short-lived due to a merger. Since then I’ve spent the majority of the last decade in corporate business consulting, specifically customer relationship marketing where I helped companies solve a variety of problems. Now I’m an entrepreneur. Outside of work, I love photography, anything athletic or outdoors, cars, woodworking, and a good whiskey.

What was the catalyst for StyleSeek? How would you describe the platform?
StyleSeek is the culmination of three growing trends: menswear, social media and personalization. We’ve all seen menswear blogs and Tumblrs explode in popularity over the last few years. More men are paying attention to how they dress than ever before and retailers are taking notice. StyleSeek integrates all three trends by providing the best products from retailers, big and small, with relevant blogs personalized to each user’s own style. What this means for the average guy is that we make finding your style easy.

When you go to the site, it looks incredibly clean and minimalistic but what goes on behind the scenes is actually pretty complex. We go beyond aggregating information by logically filtering every product, blog and brand to fit a user’s style. That way, guys can just see what they are interested in without having to put in any effort. Every day the entire site updates with new products, links to awesome articles like posts from you guys here at HYPEBEAST, and an ever-growing roster of brands.

Stylistically how would you describe yourself?
I guess if I had to describe my style I would say it’s a mix of classic Americana mixed with smaller niche brands. I could wear beat up denim, a great pair of shoes, nice watch, and a T-shirt everyday…and I generally do right now; it’s hot out and I want to be comfortable, it’s definitely a perk of working in a start-up.

I really tend to focus on fit and overall quality when I make purchases. I’m a huge fan of footwear and I’d say they’re my one addiction in terms of clothing, maybe jackets too. Basically, I just try to look great without standing out — simple but classic.

Based on your upbringing in the Midwest, how did it affect your outlook on fashion and accessibility?
Growing up in Iowa we had Jordans, the new Polo stuff, just less of it. Shopping and trying to get on that newest trend wasn’t always an option. Plus, you have to remember, when I grew up there weren’t cell phones or the internet. I had to go on road trips with friends to Chicago to see what was cool. We didn’t have websites posting trends from the street the same day. My friends and I tried to determine what we thought was cool on our own, whether it was sneakers, running shoes, or what denim to buy. I guess my outlook was always to find what I really wanted, not just buy into the quick fad or something that just didn’t look right for me.

What was the fundamental problem out there that StyleSeek was hoping to solve upon its conception?
Men want to dress better but it’s not that easy to find what you’re looking for. There is so much information and opinion on the internet now that it’s impossible to process it all. Men have questions, but don’t know where to look and in most cases don’t want to invest a lot of time to find the answer.

Most guys in America don’t have a clue what selvage denim or a Goodyear welt is, let alone why they should care. They shop out of necessity or for occasions, they buy clothing when it wears out, when they have a new job, or when they have to attend a wedding.

StyleSeek helps you find your style and optimize it to work for you. We give you context and recommendations for finding more of what you like and let you decide on the best purchase. We help you without getting in the way.

Can you speak a little about the team you’ve compiled?
StyleSeek’s greatest strength is our team. We are radically different and vastly diverse in our styles and experiences. We have a NASA rocket scientist as a CEO, an MIT MBA CFO, team members with extensive business, strategy, finance and marketing backgrounds, and even a FIDM professor who has taught fashion for the last decade. We also have an extremely talented tech team with rock star developers who make all of our wild ideas come to fruition. Together our varied skill-set and ability to work towards a common goal is what will keep us fresh and striving to make the best product.

What sort of experience does StyleSeek offer that other similar, product-based platforms don’t?
It really comes down to finding style; we go to extensive lengths to help curate and create large categories of clothing based on style. We find products, brands and content to make everything relevant one-by-one. When you find an item inside StyleSeek, you’re enabled to find as much information as you want. You can find similar styled products from other brands, different priced alternatives, and even related content to help you make a better-informed decision. It’s really the style and the context – no longer are you just looking at a product, you’re getting the entire story.
Another thing we are really focused on is a number of social impact initiatives that we find important to maintain. For instance, I’m super proud of the huge amount of products featured that are made in the USA, actually more than 10x the industry average. Things like this will keep us looking for new brands, and finding amazing stories to show our users while growing U.S. manufacturing.

How would you describe Chicago’s start-up scene?
We’re excited to be a part of the Chicago start-up scene. It’s in a really exciting growth stage and starting to get a lot of respect from firms on the coasts as well as internationally. A couple months ago, we presented StyleSeek in front of 500 people at a monthly start-up event called Technori, and our offices are also located in a brand new collaborative work environment called Catapult. We’re working side-by-side with amazing companies, which provides a great setting for exploring new ideas. It is a growing community of down-to-earth entrepreneurs.

What are your thoughts on the current fashion start-up scene?
There are a lot of fashion start-ups that have been really successful, even within the menswear industry, but we are really the first to combine personalization through technology with menswear. There is a ton of room for innovation in the industry and I hope that we can lead and become a great source for guys to find their style.

What are some of the major steps to overcome in regards to growth?
The main challenge will be continually updating the blog content and products on the site. Our style team finds the best content from the web, and then manually enters every single link or product into our system. It’s a very subjective and time-intensive process, but it ensures a high standard of quality for everything on StyleSeek. So far there’s been a lot of late nights, and we have to solve scaling issues from both a content and technical perspective. We know the steps to overcome this, and we just have to keep hiring amazing engineers, and people that live and breathe menswear.