The Proper Gentleman handmade leather goods.
(Photo by Jimmy Compton)

Handmade Leather Goods With The Proper Gentleman

Here at Skillset, we love good stories about people busting their asses to make something handmade and unique. Makers that pour their hearts and souls into their products, creating fan bases that are rabid.

Jimmy Compton is a U.S. Army soldier turned contractor turned entrepreneur. He’s quickly becoming known for his handmade, incredibly detailed leather work and his brand, The Proper Gentleman. We sat down with Jimmy at his home/office/workshop to learn more about the business, the products and his approach to growing a brand. 

Humble Beginnings

SS: Is this your first company? Give us the quick backstory.

JC: I grew up in southeast Oklahoma and had a pretty rough childhood. I got mixed up with the wrong crowd, doing the wrong stuff, and I just decided I needed to get away from it all. I joined the Army, stayed active for nine years, went to Iraq and got out in 2004. From 2008 to 2012, I served as a contractor in Iraq and Afghanistan.

In 2011, my two brothers died. I wanted a custom wallet so I could carry a memory of them around with me. After looking at some custom makers, I just made the wallet myself. I posted a picture of it on my Facebook page, and the next day, I had $1,200 in orders. It’s been like that ever since. 

SS: Did you teach yourself?

JC: I took a few classes at first. I think that if you’re artistically inclined, once you get the basic stuff mastered, you can say, “Ah, well, this is how that works and how this works.” From there, it’s like a wildfire. You can see the possibilities in anything, and it’s just a LOT of time sitting at the table. 

The Business Plan

SS: Where did the name come from?

JC: I wanted to create an image that represented my mindset about being a straight-up guy. I had the idea that back in the 1920s if someone screwed you over, you could take that guy out in the street and knock his teeth out. Everything would be good then, right? So, that’s where the idea for the logo—the bowler hat with a mustache—came from. He’s just a 1920s tough guy that is going to handle business one way or the other. We’re going to do it on the straight-up or straight-out, you know? 

Handmade leather wallet from The Proper Gentleman.
(Photo by Jimmy Compton)

SS: How do you determine what your next piece will be? What does your creative process look like?

Inspirational Moments

JC: My mind never shuts off. Just this morning, while I was in the shower! I had ideas for three different improvements that I could make for a woman’s wallet. Once I can picture it, it’s always there. I could sketch it, but that’s just 10 minutes going to waste drawing something. I just sit down and do it. 

SS: Are you only going to produce custom work, or will you have a full production line of The Proper Gentleman leather goods?

JC: No, I’m getting away from a lot of custom work. It takes up a lot of time, and when I’m working on a custom piece, no other work is getting done. Also, it can fatigue the brain. It’s like playing in a band and having to write a new song every single day. I have to build the brand. Ultimately, I’m not doing all this for me. I’m doing this so that my son and daughter will have something in the future. 

SS: What’s your future vision for The Proper Gentleman? Is there going to be a custom leather shop on every corner?

JC: That question is probably the toughest question I’ve had for myself. There’s a part of me that wants to take this and compete with companies like Eddie Bauer and American Eagle. I want to have a franchise of stores. I also want to be a curator, where I just work with other makers and help them bring some of their stuff to market. 

Unmatched Style

SS: What sets The Proper Gentleman apart from a lot of those other lifestyle clothing and coffee vetrepreneur brands that you see on social media nowadays?

JC: I just try to do everything with the mindset of “If I’m interacting with a company, how I would want to be treated?” I want to be relatable, but I don’t talk much about my background out on Instagram. Actually,I don’t talk about my upbringing, and I don’t flaunt the fact that I’m a veteran. I want people to buy my stuff because they like the stuff—not because of my persona—which is what you see a lot. Being a soldier was just something I did as a part of my life. Now, I’m here, doing this. 

SS: What’s next? What can we expect from The Proper Gentleman in 2019?

JC: I really want everyone to have a Proper Gentleman wallet, but I don’t want everyone to have to pay 500 bucks. So, I’m trying to get my product line established, get that going, and then expand it from there. I’ll be getting a few equipment upgrades to help with production. I’m going to add a couple people to the team. This year is all about structure. 

You can find the complete line of Proper Gentleman products and apparel at Interact with @thepropergentleman on social media.

For more on the hand-crafted bespoke lifestyle, check out our podcast Skillset Live!  Get in on the conversation on our social media pages or pick up a back issue at

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