When you think about the type of people that are poised to disrupt the shoe business, your mind doesn’t immediately go to an accountant. But that is just what Jack Erwin co-founder Lane Gerson was prior to launching the footwear startup.

Like many ecommerce startups, Jack Erwin began because its founders, Gerson and Ariel Nelson, couldn’t find something they were looking for in the marketplace so they decided to create it themselves. In this case, it was clean yet stylish dress shoes that didn’t cost $500 but looked like they did.

There was another agenda as well. Jack Erwin was about upending the staid idea of “dress shoes.” While the sneaker business has grown significantly in recent years—and it is now more acceptable than ever to wear them to the office or a wedding—Gerson wanted to show that the traditional leather lace-up or loafer didn’t have to be worn at formal and stuffy occasions. Not surprisingly, employees at Jack Erwin all wear the brand’s shoes (even the women). What is surprising is how, given the diverse styles of the employees, from preppy to modern, everyone is able to wear them in a way that seems distinctly personal.

The company launched in 2013 and has grown steadily since, pulling in $2 million its first year and $5 million its second. The shoes, which are handstitched using traditional techniques in Spain and Portugal, read like a greatest hits of men’s footwear, ranging from Chelsea boots to cap-toe Oxfords to wingtips. New styles, like the recently released driving loafer dubbed the Parker, roll out regularly.

We spoke to Gerson to talk about his transition from accountant to shoe executive, the death of #menswear, and which of his models he’d want to wear for an entire month.

Where did the idea to start Jack Erwin come from?
I’ve always loved fashion and appreciated simple, clean things. My first day in college, people were wearing Diesel jeans and they cost 100 bucks. I was like, I will never spend $100 on a pair of jeans. Before I knew it, jeans were the cheapest thing out there. Shirts were $300, sweatpants were $500. Shoes were a particular pain point. There was no brand offering well-priced, simple shoes. My co-founder Ariel had a wedding and we were looking for shoes. There was nothing good out there for less than $500, and everything that we could afford wasn’t what we were looking for. Naively, we thought that if we could figure out a way to make beautiful shoes with elevated materials and craftsmanship and offer them for about $200, that could be a business.

Did you have any background in shoes or fashion?
I was an accountant by trade. I worked for Price Waterhouse, then I worked for a real estate investment firm and worked in finance for a couple small businesses. My business partner was in beverage distribution. Neither one of us had a fashion background. We’ve always just had a passion for product.

The #menswear trend of guys dressing more formally has faded. How do you feel about that?
In a lot of ways we’re excited about it. When we built this brand it was never about suits and ties and pocket squares. It was not for the dapper guy. Well-made quality shoes have a history of being intimidating. Men don’t know what to do with them. They feel they have to wear them as dress shoes. No one is making this type of product approachable. For us it was about trying to remove the stigma and showcase how amazing a pair of shoes can be. They can be more casual and laidback. I wear skinny jeans and a T-shirt everyday and I wear all of our shoes. It’s a good look. Men are starting to live more casual lives and sneakers are getting a lot of play right now. But people want a pair of shoes that they can wear to coffee in the morning, a meeting in the afternoon, and dinner at night and feel comfortable and presentable at all those things. There wasn’t really a brand that embraced that. Sneakers are fun. But men want to evolve and there’s really no place to evolve to. After you go from a pair of Converse All Stars to a nice pair of sneakers and then want to be more sophisticated, I think we’re that next step.

Designing a pair of Jack Erwin boots

Designing a pair of Jack Erwin boots

How would you describe the design aesthetic of the shoes?
It’s rooted in heritage. All of our patterns are inspired by classic men’s shoes but we try to streamline them and make them more modern. The Joe does a great job of this. It’s a sleek cap toe. With our boat shoe, we took a shoe that has a shitkicker stigma to it—a shoe to take out the garbage—and elevated it. These classic patterns are beautiful and we should respect them but with a new take.

How do you come up with the names?
Originally we had five shoes, the Joe, the Adam, the Abe, the Jake, and the Ike. They were all modern takes on biblical names. So Ike is Isaac and Abe is Abraham. Lately it’s been, “Hey guys around the office, who has some names?” and we see what sticks.

The most recent releases are the boat shoe and the driving shoe. Those are more casual silhouettes than your earlier offerings. What influenced that shift?
The point of the company was not to be a strict dress shoe company. We want to extend from the driver all the way to the tuxedo shoe and fill in that whole part of your wardrobe. There’s a lot for us to do in that casual sphere while still using great materials and great construction.

What are you doing in terms of materials and construction that sets you apart?
All of our components are sourced by us. We design all of our own lasts, the form that the shoe is built on. Factories traditionally maintain a bunch of lasts that they’ve used over the years. A lot of manufacturers just go and find one and use that, but we develop all of ours with a lastmaker. All of our patterns are designed by us in house. We select all of our leathers. We make sure that every component that goes into our shoes is something that we have a say in. It’s small details. On the boat shoe we designed our own siping, which are the marks on the bottom of the shoe to give an elevated appeal. It’s not really visible, but it’s worth it to us.

via Jack Erwin

via Jack Erwin

Who do you see the brand competing against?
Some of the older dress shoe companies like Allen Edmonds, the Cole Haans of the world and Johnston & Murphys. Then you look at some of these companies doing elevated casual sneakers and we want to compete in that space as well. We’re a young, upcoming brand. A lot of our competitors are targeted at an older demographic.

How would you describe your own personal style?
I am about fit in a lot of ways. I wear subdued colors, dark navys, browns and blacks. But I like to mix up fit, skinnier pants with a loose fitting shirts and vice versa. I’m pretty casual in my day to day, but I try to be pretty clean and simple.

Do you have any go-to items in your closet?
I’m a huge accessories fan. I’m into great sweaters. Living in New York, I’m really down with great oversized coats. I love shoes obviously. I think belts are really interesting. I’m a big Uniqlo fan for my clothes and then I like to thoroughly explore on the accessories.

How many pairs of shoes do you own?
I only wear running shoes and our shoes. My whole closet is a pair of Nikes and our shoes. I think I have most of the pairs that we’ve developed so far. I have 10 or 15 pairs in rotation and I switch it up.

How do you figure out your outfit each day?
I’ve gotten weirder. At this point I lay out my clothes the night before which I never used to do. I think I do it because I am the first up in the morning. I feel like I go for whatever’s on top of the drawer. I’m pretty uniform-ish. Right now I’m wearing blue jeans and a blue collared shirt. And tomorrow I might wear black jeans and a black T-shirt. I’m pretty consistent.

Who do you look to for style inspiration?
There’s a lot of old-school guys who wore great clothes and wore them really well. Back in the day it was more dressed up than it is today. The McQueens of the world and that era was a nice time for menswear. Men took care of themselves and cared about what they put on. That’s kind of why we built the company. We respected all of that and wanted to bring that into today’s world.

If you had to pick one of your shoes to wear for a month straight, what would it be?
Great question. What do I have to do in these shoes?

You have to live your life, but you can still have your running shoes for exercise.
I think it would be the Dylan, the plain-toe blucher.

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