Sugarloaf Social Club is…well, we’ll get to that later. We’ve covered SSC’s designs and collaborations in the past — from the Pimento Loafwich, to Don White wedges, to “Cody the Super Pack.”

Now, the crew are joining forces with none other than Original Penguin as the iconic clothing brand prepares to return to the golf space.

I talked to Sugarloaf co-founder Ian Gilley (pictured below) about the upcoming collaboration, dug into the club story, mulled over interesting developments in the world of golf apparel and equipment, and, of course, Instagram, too.

BA: For GolfWRXers who may not have heard of you, talk a little bit about SSC’s background and history.

IG: Sure. Sugarloaf Social Club was started in 2011 by me and my two roommates from college. In our final year at Rollins, we were looking at each other, and we started to get a little nostalgic, knowing we were heading to three different cities and we wouldn’t have that camaraderie, talking and playing golf, anymore.

I’ve always liked the idea of kind of branding something and figuring out what it is later. We were playing this course called Sugarloaf Mountain. It was in northwest Orlando, it doesn’t exist anymore–a really cool, Coore and Crenshaw course. Earthy, affordable,minimalist place that kind of encapsulated everything we’re about for a golf course. And I was like, “Why don’t we call ourselves something? Let’s just call ourselves Sugarloaf Social Club.” I thought it’d be a little umbrella over our friend group, and it’d give us some incentive to keep in touch.

That was May of 2011. We all went our separate ways. At that point it was just a private Facebook group, and the idea was that we’d add a few “members” here and there along the way. Fast-forward to 2018, and SSC is a golf society that has, like, 25 members at its core [and 11.6K followers on Instagram].

The other huge pillars of the Sugarloaf story….Four years ago, when Instagram was new on the scene, we saw it as an opportunity to share some photos and stories from our travels, have a voice, define an aesthetic, and share what we thought was cool about golf.

Fast-forward a few more years, maybe around 2015, we have a couple of dozen guys and we wanted to make some club swag. But it turns out, minimums for logo hats, per se, are a lot higher than that, so we had extra. So, like, my buddy in the office wants a hat, and he’d PayPal me, and I’d give him one. Or, somebody out in California wants one, he’d send money and I’d ship one out. But I got kind of tired of one-by-one doling out items and filling out labels on USPS.com, and I needed a streamlined, efficient way to sell merchandise, so that’s when we started the website.

BA: So that’s an interesting point, here, the growth and move into selling merchandise was totally organic? You didn’t set out to be an apparel company…

IG: Yeah, totally. We just do stuff that we think is cool. If we want to do a cool hat, then we’d love to share that. I mean, it was just last January that we launched the website, and that was primarily to handle getting gear to people. Then, things like the Pimento Loafwich caught fire. But it’s really been this fun project of just sharing cool gear that we wanted to wear ourselves.

The focus has always been on small batch, limited releases, exclusive stuff. We don’t want to buy 100 hats. We only want to do a couple of dozen. And there’s something inherently special if people are going to spend their hard-earned money, there should be some intrinsic value and it shouldn’t be something that everyone is going to have.

BA: The story from a merchandise standpoint is interesting. In one sense, it looks like brilliant market research, and that there was something out there untapped that you tapped into, and on the other it looks kind of random.

IG: That’s what’s fun about it. There’s an inherent randomness and sporadicness: If we have a cool idea, we make a logo file that day and start the process of getting gear. And I’m sure your next thought is about something like the Don White wedges where we’re able to do these cool small batch things. There, we just wanted to give credence to someone’s legacy who was undervalued for many years. Fundamentally, we love doing collaborations.

BA: Which is a nice lead in to the work with Penguin…

IG: Yeah. This time last year, they saw the pimento logo, and they thought it resonated with them as a brand that was tapping into a heritage element, but in a modern way, and has fun. The pimento cheese sandwich is this fun, quirky icon, but to the hardcore golfer, it says a lot…without being overtly “golfy.” Everything we make, I want to make sure it works on a street level or can work at the bar.

BA: Let’s detour to the Pimento Loafwich for a minute. You’re utilizing such a loaded symbol, and the execution of it–being almost cartoonish–it kind of encapsulates what you’re going for what you’re about, to my mind. But back to the Penguin partnership.

IG: Right. So, they came to us this time last year. I couldn’t believe it when we got the direct message on Instagram. It was like, “Really? This Fortune 500 company [Penguin parent Perry Ellis International] wants to work with this small Instagram account?” But their long-term vision is, they’re getting back into golf. They’re single-handedly the greatest golf heritage brand out there. Nicklaus. Palmer. Chi-Chi. Penguin was the sport shirt for the golfing man for years and years.

They owned that sartorial shirt market for decades…probably from 1955 to 1975, and they were still kicking in the 80s, but they they got away from it for a few decades. So they’re seeing a huge opportunity to get back to that and kind of do something authentic. But that’s a big ask to get ingratiated with a generation who doesn’t know much about you. And they saw Sugarloaf as an entity that could give them instant grassroots credibility with the golf enthusiast.

Their proposal was to do a co-branded collaboration that would launch a month before their bigger golf line to get back in the space.

BA: What has the process of developing the pieces been like?

IG: It’s been amazing. They’ve given us full authority to design every inch of these products. I’ve been to New York probably six times this past year, working with the head designer, working with the president, sitting down for hours at a time to design, like, a simple white shirt. You think that’d be easy, right? Everything we do, we’re obsessed with the details. So, like, with a simple white shirt, we’re looking for elements that could make it uniquely Sugarloaf. We wanted to pick things we thought we were really cool.

Two examples: The specific Penguin logo used on our shirts, you’ll notice it’s colored. That’s a specific logo from the 50s when color television was becoming popular. Then, going through the archives, I noticed some shirts with the Munsingwear “M” stitched in the placard. I thought, “We can’t forget about Munsingwear, the 150-year-old parent company.” So, we wanted a little ode to that side of the heritage. And the top button has a little red stitching, which is a Sugarloaf thread. So there are these really cool hidden elements that we thought were fun. And there are only 100 pieces of each shirt made, and they’re individually numbered.

But there are four shirts and one jacket in the collection. At the end of the 60s, these guys are wearing very classic palettes. Probably 80 percent of the Tour was wearing white polos. The other colors that you’d find in the archives were, like, different types of navy. So we have a rich, dress blue navy polo. The third shirt is called “double cream.” Back in the day, there were a lot of cream and almost brown tones. The fourth shirt is striped shirt, and it is an exact pattern replica of something from their archives, because the line needed a little pop.

The Ratner jacket is a classic silhouette that we really loved. I thought it would be cool to have a zip-in hood in the collar, because that can come in handy from time to time. We wanted to do something that looked inherently old school, because a lot of windbreaker jackets these days look hyper-modern and futuristic, so we wanted to do something old school using modern fabric.

BA: Obviously, this is a good thing for you guys, and really clever work on Penguin’s part using this as a lead-in to a larger launch.

IG: Yeah. You have to hand them a ton of credit for taking that risk and having some awesome foresight. That’s something you wouldn’t see a lot from a huge, publicly traded company.

BA: Right. You wouldn’t expect the flexibility or the fluidity and maybe not the experimentation. Pretty cool. You guys are so tied to Instagram, and I certainly respect the way you’ve made that the core of your presence and haven’t tried to be everywhere and active on all channels. And it’s been a really solid, steady presence for the past couple of years. There has been some really cool stuff happening in the golf content space during that time.

IG: We definitely saw the power in being able to reach people directly and to be really niche. You look at, like, the No Laying Up guys, and they’ve captured an interesting niche. The Fried Egg guys, they do their thing. There’s all this room out there to have your own lane. The number of followers isn’t something we’re worried about. It’s about the quality of followers and taking care of those followers, you know, we’re not doing any weird tactics to get more followers or using tons of hashtags. It’s about taking care of our community and making sure they feel heard. I want Sugarloaf to be the last, best place of the golf internet. We want you to find it yourself.

BA: Cool. Let’s circle back to the Don White irons and wedges. 95 percent of what you’ve done has been on the apparel and accessories side of things. What did you see there? What has the reaction been?

IG: It was similar to all our products in that we only think are cool, and unique, and has a history to it. So, when the opportunity presented itself to work with Don White, who wasn’t doing much post-Scratch, we were excited. Don White is a living legend, and he’s underappreciated. It wasn’t about making money for anyone, but making sure Don White wasn’t forgotten in this modern context where there is such an affinity for custom clubs.

BA: I’ll be interested to see what you guys do on the equipment front down the line, because that’s a market that’s not totally being catered to.

IG: Definitely. I think you could envision our next project with Patrick [Boyd] and Don might be looking at a half-set concept, as getting a whole set from them is inherently expensive. But it’s also makes sense in the whole shifting dynamics of golf at the moment. Maybe we get into promoting pre-built half sets that are well-spaced together.

BA: That dovetails with a couple of trends both in golf and in larger society. And obviously, high quality means higher price. It’s something that makes sense, but you can understand why it’s not in major OEMs’ interest to pursue it. Still, on a smaller scale…

IG: I think that’s definitely something that’s coming down the line. I’ve gone back to old MacGregor irons. I’ve got my MacGregor irons. I’m using a Titleist 945 driver, and I play just as bad with those. Talking about gear and tech, the super-quantifiable advancement is the ball, so of course I’m not out there using a balata.

But in this age of social media and ubiquitousness of brands, people have the desire to feel like an individual. I think you’ll see a lot more trends along those lines.

BA: It’s wide open in a way it historically hasn’t been. Just look at the Tour, which is encouraging from “the Tour leads and everyone follows” idea. Stampings. Paint fills. Grinds. Grips. Covers.

And there are multiple types of equipment enthusiast, right? Obviously, there’s the guy who wants the latest and greatest and needs to see demonstrated improvement on a launch monitor. But there’s also the enthusiast who’s interested in history and great legacy clubs, collects old blades, etc. None of which is to talk about the hickory junkies. So there are plenty of interesting affinity groups huddled under the equipment junkie umbrella.

IG: Yeah. We’re not always buying the latest and greatest, but that’s what I think is so amazing about golf. If you’re a tech guy, there’s a space for you. If you like history and travel, there’s a space for you. If you just like hanging out with buddies, you’ve got it. If you like exercise, there’s a space for you. Going back to where Sugarloaf fits in, we’ve got our little niche, and that’s just fine.

BA: Awesome. Do you want to close with a bit of what’s on tap for Sugarloaf?

IG: Well, last year, we did a physical event [the Jamboree] with Holderness & Bourne at Yale [University Golf Course] which was a huge success. So, we’re definitely going to continue doing physical events. We’re considering scramble outings that have some unique elements to them. We’re going to go to Sweetens Cove, which is the darling of the 9-hole movement. We’ll play the traditional routing [for nine holes], then turn it into cross country-style golf, and we think that’ll be an interesting way to do outings differently.

We’re going to have a physical pop-up in mid-March in D.C. We’re trying to think, “What would a physical Sugarloaf shopping experience look like?” and looking for cool places to do that. And of course, we’ll have exclusive merchandise just at those locations. We’re also going to do a pop-up with a few different brands in the Hamptons during the U.S. Open.

We have a collaboration on deck with a brand called Rowing Blazers. They’re one of my favorite new brands. Similar to Sugarloaf, they’re really into rowing culture and the clubs and the pomp and circumstance of team colors and club blazers. We’ll try to put that concept into the golf space for the Ryder Cup. Those are just a couple of the things we have on deck, and of course, we have fun products always, always in the pipeline.

Check out the Sugarloaf shop and the Penguin golf site.