Let’s face it, figuring what to wear every day can be a pain. Sure, if you’re the kind of guy that likes to peacock around, each morning provides an opportunity to stunt. But those fashion risks can easily turn into fashion fails. And then you forever become known in the office as the guy who wore the floral brocade blazer to the quarterly meeting.

The flip side is to go the Zuckerberg and Jobs route and create a personal “uniform” and wear the exact same thing every day. The challenge there is that your style goes, to paraphrase Drake, from 100 to 0 real quick.

The answer, as with most things, lies in the middle. Even if they don’t like to admit it, most guys want to look good. The problem is that a lot of guys don’t know how to pull that off and don’t want to spend the time and effort necessary to learn.

Courtesy Mylo

Courtesy Mylo

That’s where Mylo comes in. Founded by entrepreneur Daniel Eckler, the app claims to be “the simplest way for men to dress well.” The way it works is a user tells Mylo what clothes he already owns based on a list of approximately 75 timeless classics such as a white button down shirt and navy blazer. Then the app will pull together a series of looks after factoring in the occasion (work, wedding, etc.) and weather (it can sync to your location).

Then if you need to pick up some new clothes to fill out your profile, Mylo will make recommendations based on how many new outfits each item will open up and allow you to purchase them through your phone. Based in Toronto, the startup plans to launch the app in the fall and is currently accepting signups for access.

We spoke with Eckler about how he came up with the idea for Mylo, the current state of menswear, and how it all comes back to Clueless.

What was your previous experience in the menswear space prior to starting Mylo?
When I was in university I started a streetwear blog called FormatMag.com. At that time, Hypebeast and a couple others existed but they mostly focused on product releases. There wasn’t really a great place for in-depth stories about what was going on. This was around eight years ago. I grew that into eight to 10 different men’s fashion and lifestyle blogs that merged into a hub called EveryGuyed. Ironically, I learned that people weren’t interested in reading in-depth stories. So I sold the company and decided to build a new company that was a platform for bookmarking images. That turned into Piccsy. We launched around the same time as Pinterest and were actually ahead of them for quite awhile. Then they obviously just destroyed us and became what they are today. When I realized that Pinterest and Tumblr had the No. 1 and 2 spots in that category, I decided it was time to find a new opportunity and started thinking about what Mylo has become.

When did you first have the idea of creating Mylo?
I had the idea maybe four years ago to do a stylist [app] for men. That was all the idea was. When I decided to sell Piccsy, I went to Asia for two months to think about what I wanted to do. I realized a big part of what inspires me is a philosophy centered around encouraging people to live simply and, in turn hopefully, happily. I was very much inspired by the [Japanese] company Muji. I decided I wanted to start a company based on those values and aesthetics but leveraging new technology and cultural trends. I released a few products on Kickstarter, selling homewares under the name Mijlo. Then one day it occurred to me that I had this idea for this stylist app and I realized that merging that with this philosophy and aesthetic was exactly what I should be doing. It just made total sense given where we are and given the void, to be honest, in the market today.

What’s your take on the current state of menswear?
I think a lot more about the combination of menswear and technology as opposed to menswear as a fashion thing. A lot of the investment that’s going into fashion startups is going into companies that are really just traditional companies that are using the internet as their primary distribution and marketing tool. That’s not a novel idea. And now all those companies that started online are now opening up stores. So there’s very very little difference between these companies that are popping up online and their contemporaries that started in brick and mortar. I love a lot of these companies, but are they doing anything innovative or interesting technically? I don’t really think so for the most part. Mylo is a really interesting opportunity because we are doing something interesting technically and trying to push the limits of what’s possible with fashion online.

How is the app able to figure out what clothes work with others?
This is the 20th anniversary of Clueless this year and people have been waiting for the Clueless closet for 20 years, this thing in their house that analyzes all their clothes and shows them what to wear and what not to wear. A lot of people have actually tried to build that for women but I think the challenge that most people have undergone is if you allow people to include any piece in their wardrobe the technology becomes a million times more difficult. That’s where taking the philosophy of Mylo really helped us a lot in simplifying the technical problem. Here’s these 75 or a 100 pieces that are the canonical staples for men that people have been saying men should own for 50 years. If you just pick those pieces it becomes much easier to fit them all together with technology. So we simplified the problem and we’re starting with that.

Do you think this is going to make people consume less by realizing the versatility of the clothes they already own?
That’s very much what we’re trying to do. There’s all sorts of reasons that buying lots of stuff is not a great idea whether that’s wasting money or psychologically just being in a constant state of want or buying all these things and not knowing what to do with them. All the classic men’s pieces really do go well together and are super versatile. If you get high quality versions of them they’re going to last a long time. It’s just a really educated way of shopping for men. The success of companies like Zara and H&M, which I think do a great job with what they do, have changed the thinking around how we should shop for clothes. That’s good for certain reasons and bad for certain reasons. I think we’re trying to show the other side of that.

Why do you think guys need an app like Mylo?
What’s been surprising to me is the amount of guys that I talk to that are pretty poorly dressed to the degree that they don’t even think about it. They wear the same bad clothes they’ve been wearing since college and literally have never bought anything since then. They have this anti-fashion bent. But when you dig a little deeper with them, they say things like “I actually do want to look a little bit better, I’m just intimidated and don’t know where to begin.” For those guys, this is a great way to hold their hand through it. And for guys that do dress well already, this is an easy place to buy staples, and, with the tap of a button, they know they can get a new pair of white sneakers.

Will guys still be able to personalize their own style with Mylo?
That is another challenge that we have been working with. Personally, the way that I learned to dress was I found a style very early on that I was comfortable with and expressed who I was. It wasn’t until I was like 25 that I bought a white button-up, which is the first thing that most guys should probably buy. I think the better way to do it if you’re coming from a place of not knowing anything is to start by buying the staples. Either that’s all you own and you’re comfortable with that, or as a result of buying and learning about those you start to venture out a little bit and find the way in which you want to express yourself and tweak things and throw in extra pieces that really identify who you are. I think the right way for most men to build a wardrobe, regardless of who they are and how they want to present themselves, is to have those staple pieces to begin with and then find a unique angle from there.

Courtesy Mylo

Courtesy Mylo

Does that present an issue where the app could educate people to the point that they don’t need it anymore?
It’s tough to say. One thing that we think about that—and I’m not sure if we’ll implement this—is here’s the 75 staple pieces that everyone should own. Once you own enough of those and can pick what your style is, tell us and then maybe there’s capsule collections of five or 10 pieces that shoot off in different directions and have the staple pieces for that particular type of person. If it’s a streetwear guy, there’s Jordans in there or whatever. That said I’m not totally sure. We’re still thinking about that and I don’t know where it’s headed.

How would you describe your own personal style?
I’d say classic pieces but always with a little twist. Today, for example, I’m wearing a gray T-shirt and a light blue ripped jean and a white Nike blazer similar to the Adidas Stan Smiths that everyone is wearing. For me it’s very much about comfort.

Aside from Mylo, are there any style apps that you use a lot?
I’ve played with pretty much everything on the market. I’m not really impressed with any of them to be honest. There’s no one in the men’s category that I’m very excited about. For what they do, they’re doing a good job, but it’s not stuff that excites me personally.

Justin Tejada is a writer and editor based in New York City. Follow him on Twitter at @just_tejada.