It only took about five minutes of conversation for Chris Stapleton and the team behind his Lucchese collection to convince me to take my boots off. And it wasn't until I'd stood up after our conversation that I'd realized I'd never actually put them back on.
Stapleton—fittingly, for one of country's biggest acts of the past decade—has a real eye for detail. I'd mentioned that I'd bought myself this pair of Luccheses (my only pair) on eBay for $100 as a college graduation present for myself. Instantly, he said I was wearing the same boot getting reissued as the San Antonio in this collection.
Doug Kindy, Lucchese president and CEO, and Trey Gilmore, Lucchese men's director of product development, confirmed the theory—the classic cord pattern and mule-ear pull straps being the dead giveaway. Then, they wanted to date the boot, so I pulled it off, and they read the stamps on the inside: April 1998.
All this to say: Stapleton himself has a collectors eye, which spans cowboy boots, guitars, pocket knives, and cars. He's got as keen an eye for Lucchese boots as the folks running the brand, so there's really no one better to be the face and creative mind behind a line of boots. Stapleton's style skews classic, and all three of the boots he just put out with the brand scream that.
For the launch of the collection at Old Glory, a Nashville speakeasy, Stapleton spoke with Esquire about his taste, how the collection came about, and what's been a huge past year for the eight-time Grammy winner. This interview has been edited and condensed.
SHOP LUCCHESE X CHRIS STAPLETON
ESQUIRE: So I've heard a lot about you hunting down old Lucchese boots on eBay, in thrift stores, antique malls, stuff like that. Do you remember your first pair?
CHRIS STAPLETON: The first pair of Luccheses that I owned [the Lucchese team] built for me. I should have worn those boots tonight. But, you know, they were kind enough to give me a tour of the factory. I was on a radio tour. I wasn't anybody, really. But, they offered me a pair of boots. And I said, "You know, I just want something I can wear every day."
I mishmashed some different features they had in the room—they had this really nice room, you know like a Charlie and the Chocolate Factory, Willy Wonka room for boots, and that became the first pair of Luccheses that I owned. I owned some other boots, I'd tried on some Luccheses, but hadn't taken the dive yet. And when they built me that pair it was over. That's only brand of cowboy boots I've worn since.
THE ORIGINAL $1195 lucchese.com
OK, so the obsession really started after that?
Yeah, I started really deep diving to find old ones and showing Doug [Kindy] and saying, "How 'bout these, can you guys make these?" And that's how I got the boots that I've got on. This pair of boots, which they made me, was based on a pair of made-in-San Antonio boots, before Lucchese had moved to El Paso.
THE SAN ANTONIO $995 lucchese.com
So I bought a boot, it was a boot that looked just like this, and it was a 12B; I'm a 12D. So I bought this 12B, and I was like, well... maybe they'll stretch. And then I sent them to 'em, and I was like "Can you stretch these and make them fit? Can turn these into a 12D?" It just wasn't working. But I loved them still, so I said, "Well, can you just make them?" They said, "Yeah we can do that." So that was probably the beginnings of talking about doing some of this.
So the partnership, and this collection, kind of naturally came from that process? From you asking them to build boots that looked like old ones you liked?
Yeah it was that, kind of, revivalist aspect of taking that San Antonio boot—which we just named that one the San Antonio, in this collection, because of that. I think that kind of planted the seed for all of us. It did for me. And after we started doing that, it became collaborative.
I've also heard that when you were buying some of these old boots on the internet, you were actually bidding against folks at Lucchese, who wanted boots for the archive.
Well, I didn't know I was doing that! [Laughs]
It's just some random username on the other end.
And half the time I'd just say, "Hey, I just bought these cool boots, you should check them out." Or I'd leave them with them some way. I do that with some other companies I work with, too. Because I love stuff like that, and I think, "Why aren't you still making this thing?" And then they go, "Well, maybe we should do." And that's how a collection like these boots come to be... Or they come to re-be.
What about the suede boot, specifically? They're called the Old Friend in the collection, how did Italian suede get into the collection?
How I got these is funny. Something happened, and I was on the road. There's a suede boot Lucchese made called the Romeo, but the toe's different. I was in Texas—thankfully—and I had left my boots at home to play a show, so I was on the road and didn't have a pair of boots.
I called someone at Lucchese and said "Do you guys have a store or someplace near me I could go get a pair of boots?" And I went in and I bought a pair of the Romeo boots to wear for the show. That's how I got into wearing suede, and I always said to [the Lucchese team], "Someday, you know, I like this other toe better, if I could have that on this boot." But that's the pair of boots that I wore for the 2015 CMAs performance with Justin Timberlake.
So this collection really did spring up from you building your own boots.
Yeah, I mean, it was years-long process of accidentally designing these things. For me, the form of these things came out of my need for them to function for me in the way that I use them. You know, I like boots that are everyday boots, something that you can wear every day. Rattlesnake's cool and crocodile's cool. Those boots are like art pieces to me, but I always gravitate to things like this that I could wear at any point in time.
It really just came from that everybody at Lucchese going, "Hey, you need a pair of boots? What kind of boots do you like?" And it was something close to these three. So when it came time for this, and it was like, "What do you want to do?" I said, "I'll make it easy on you. Here's three things that we've already built. I love these. Let's pick a couple colorways and go with it." I've tried to do things that I liked, but also pay homage to Lucchese as a company, and I think we've achieved that.
Have you always been this particular about the design, or craftsmanship, of the things you own?
Well listen, your boots are from '98, you bought them second hand, and they'll be your boots forever, if you want them to. Take care of them. You put a heel on them and resoled them... So yeah, I do. I do care about those things. I do care about the details of things. I care about the people that are making the things. I've been to the factory, you know. I've met every person, I think, that works in the factory. At least once, and some of them several times.
That matters to me. That kind of detail. And Lucchese is unique in that. I haven't visited every factory of the brands I work with, but they're very unique in that there's so much handmade stuff going on. Have you ever walked through the Lucchese factory?
I haven't.
You need to put that on the list, because it's something to see. I've been through car factories, different kind of factories, you know. There's a lot of automation everywhere today. But there's none of that, that I could see, at Lucchese. There might be a sewing machine that has some programmable features. But I think that's about it. Other than that, you've got folks working on turn-of-the-century machines. They manufacture parts to keep those machines working, because that's what they like to use. It's just awesome, and it makes the boots more awesome—knowing how they're made.
And away from boots, you're kinda just adding a full collection into what's already been a huge year or two for you, probably culminated with that National Anthem at the Super Bowl. It was really well regarded, there were those great shots of everyone tearing up. And Nick Sirianni fully crying became a meme in and of itself. How was that on a personal level. Were you nervous leading up?
One hundred percent. I mean, if anybody told you that they weren't gonna be nervous singing the National Anthem at the Super Bowl, they're liars. Singing the National Anthem was nerve wracking enough. It's one of those things that if you're going to be filmed doing it, if you mess up—you mess up the melody or just anything weird happens—you're immortalized in that way, screwing up that moment.
And bit of a music nerd question, what about that black Fender that you used for that performance? It's not a guitar I'd seen you use before.
That was the backup guitar. I'd brought an old one that I was going to play, a '68 Tele that somebody had stickerbombed with an American flag. But for whatever reason, with all the broadcasts going around, that old thing had a hum. Fender had sent me that guitar, but that's a brand new guitar. And it's another great reissue that they're making. It's an early '70s Telecaster custom, and they did a dynamite job with that. So, that was the backup, and that made the cut.
Big theme here is you always need a backup. Whether it's boots or a guitar.
Exactly, it's just like picking up those suede boots. I forgot my boots, or something didn't work out, and I needed the backup. So, I'm a big backup guy. I have a backup all the time for anything. Because I don't want to get in my situation where I have to go find boots again.
Then most recently, you won Entertainer of the Year at the ACM Awards, and that picture of you cleaning up confetti after went viral. What's the story there? Were you just killing time waiting on your car to come around?
I was walking out. The guys were cleaning up, and I asked "Hey can I hold that?" Just to blow things around, and they got a photo snapped, you know. People tell the story, I think, a little different than like I saw it. I just interrupted a bunch of guys who were actually working.
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