Designing the Ultimate Thru-Hiking Hoodie: The Story Behind Jolly Gear

The first time I saw the “Triple Crown Button Down” was in an Instagram post from Jack “Quadzilla” Jones. He was on his Calendar Year Triple Crown (CYTC), hiking the Appalachian Trail, Pacific Crest Trail, and Continental Divide Trail in less than 12 months (290 days). Besides his massive quads in the photo, his colorful sun hoodie caught my attention. I’d never seen a shirt like it and immediately looked into it in preparation for my upcoming thru-hike.

I found out that it was called the Triple Crown Button Down, and a thru-hiker named “Jolly” had created it. When I saw that there were limited quantities of each pattern, and both the small and mediums had sold out, I quickly purchased one in an extra small and hoped it would fit.

My shirt came fairly quickly and I was stoked. It fit perfectly, and there was even a handwritten note. It was a great first impression of this up-and-coming-gear company, Jolly Gear.

I had the pleasure of meeting Jolly at Trail Days in Damascus, Va., last month. After a long day of talking to thousands of people, he took the time to sit down with me to talk about his Triple Crown Button Down, the story of Jolly Gear, and the future of thru-hiking.

A ‘Jolly’ Interview With Bennett Fisher

GearJunkie: Tell us about yourself. Who is ‘Jolly’ of Jolly Gear?

Bennet Fisher: My trail name is Jolly; I’m 26. I live in Logan, Utah, but was born and raised in Alabama. I first thru-hiked the Appalachian Trail (AT) with my dad in 2015. [At the time] I knew absolutely nothing about thru-hiking. The Appalachian Trail was my first backpacking trip.

I had a huge 65L backpack. My base weight was probably like 30 pounds. Then I caught the bug of thru-hiking, and before the end of the AT, I was already planning to do the PCT.

GJ: What’s the origin story of Jolly Gear?

So, I’m getting ready for the PCT. I was thinking what do I wear? A sun hoodie or button-down? … How do you choose? I wound up with a button-down because I like to be able to unbutton it and vent. I feel like there’s a lot of benefits there. Also, a lot of sun hoodies are really tight around the neck when you do have the hood up. I was growing my hair out, and my hair is very frizzy. When you put your hood up with long or big hair, the sun hoodie doesn’t fit properly.

Anyways, I get out there in my button-down … Then I meet this guy and he was wearing a quarter-length cotton button-down with a hood, and it had a kangaroo pouch. I asked him where he got it. He said, “It’s my mom’s gardening shirt.” … So that’s where it developed.

I was also going to college at Utah State after the PCT. I finished the trial on the 15th, and school started on the 27th … There was a sewing portion in our product design class. You have to either sew two button-downs or a lined jacket, and when that came up I knew I had to sew this sun hoodie I’ve been talking about. We learned about patternmaking, so I altered a pattern and then mocked up a hood to attach to it, and I sewed that up.

Then there was COVID. LinkedIn was a graveyard; no one was hiring. I was looking for jobs after graduating and thought, this isn’t what I want to do with my life. I’ll try to make this button-down sun hoodie a thing.

So I created Jolly Gear.

GJ: Can you tell us about the Triple Crown Button Down?

Yeah, Triple Crown Button Down is my flagship product. It was the first button-down sun hoodie with a full front button for ventilation, and an attached hood with a ponytail hole, so that way you can put your hair through it. It now features cinch chords on the hood for when it’s windy, toggles to keep those in place, and reinforced thumb loops on the sleeves.

I think this was the only button-down sun hoodie, at first. Now there are a few competitors, but Jolly Gear is the only one that still allows you to unbutton and vent and roll up your cuffs, and that also has a thumb loop. We do it in fun florals and different patterns. Our fabric is 86% polyester and 14% spandex. A men’s medium garment weighs about 8 to 8.5 ounces. It is UPF 30. It has silver thread in the product, which should help reduce odor.

GJ: What did you think when you got the first samples?

The first time we got the perfect sample was when I was already hiking the CDT. We got them in Helena, Montana, going SOBO. We got eight of them and opened them up in the post office. Everyone took their shirts off and put them on, and we probably looked crazy. From Helena, which is mile 400, we had three hikers of the eight finish; everyone else either quit or got injured, but everyone who stuck through it finished — and in the Jolly Gear shirt.

My buddy — who got one of those first eight samples — even texted me with photos of him finishing his Triple Crown hike in his Triple Crown Button Down. He said when he got home and washed it, it smelled so good he wore it out on date night the first night back off-trail.

GJ: How did you design a shirt built to withstand constant use over 2,000 miles?

Backpacking and thru-hiking experience. At that point, I had done two and a half thru-hikes, so I had been wearing different hiking shirts for a while. But when designing [the Triple Crown Button Down], getting fabric samples was tough. I probably sent emails for sample requests to 10-15 manufacturers and got back these awful fabric squares that were like tent material or rain jacket material. I said, “Hey, I want to make a button-down sun hoodie,” and they didn’t get it.

I’d never owned a business so I was asking, How much does a sample cost? How few shirts can you make? It was very hard. Manufacturers were getting back to me saying you need to order 1,000 yards of fabric.

I finally got an email back from one manufacturer that said yes to a small run, and asked for photos of the sample and prototype. And they sent a package about 2 months later. I was expecting an envelope like all the other manufacturers had sent with little swatches. But this manufacturer sent us a box of sewn shirts that perfectly matched the images I sent them of my prototype, in my size. The day they arrived, I was tearing up in my living room. I could finally wear the shirt.

On the CDT, I decided if these shirts can finish, then it’s worth it. Because I didn’t want to sell a thru-hiking shirt that could not thru-hike.

GJ: Can you tell me how you pick Jolly Gear’s designs?

I’m not an artist. I had these ideas in my head, but couldn’t put them on paper. The idea behind putting patterns on it [came to me] on the PCT — the vibe where you go to a thrift store, buy a Hawaiian shirt, and you’re on vacation. That thrift shop fashion is really popular in thru-hiking: everyone wants to be unique and express themselves. But we’re forced into these technical solids.

I had seen artists on Instagram and reached out to them, asking how much would it be for a custom print. But it just didn’t feel right. And then I saw this Lite AF backpack in this paisley print, and I said, “That’s Jolly Gear.” The artist was tagged in the caption — Dan Pecci.

So, I reached out. Dan was so excited about our idea, even though he didn’t know what thru-hiking was. So I told him more about thru-hiking and thrift store fashion. He said, “I have this pattern I think you’ll really like.” He actually did a thrift shop fashion study in college and made some patterns for it.

A couple of days later, he emails me the pattern. And he did it in two colors to see which one we liked. I said, “I’ll take both.”

GJ: When did you decide you wanted to go to school for outdoor product design?

It was on the Appalachian Trail. On the AT, I got to see all of the products and gear. Tents, sleeping bags, everything has a weight, everyone has a preference. Before that, I wanted to be a marine biologist. I also worked at a gear shop after the AT. Gear reps would come in and that’s what I thought I wanted to do for work.

And then I heard about this program at Utah State for outdoor product design, and that was it. The AT is where my passion for evolving gear came from. I got into outdoor [gear] design because of how much that AT hike changed my life. So much that I wanted [a way] to help enable other people to get outside and enjoy this thing that had such an impact on me.

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GJ: Will you continue releasing limited-edition patterns? What’s on the horizon for Jolly Gear?

Yes, I think moving forward, we will move to fewer quantities and more prints. We’re going to have some year-round prints that are kind of Jolly Gear Classics and release new prints where we can be more experimental. The first year we had 250 shirts of each color. This year, we had 750 units split between short sleeves and long sleeves.

Now, we are working on new prints and new products. Check out our Instagram to see what’s coming. You also might see some hikers on the trails this year testing our samples.

GJ: Is there anything you’d like to add about Jolly Gear?

You know, it’s crazy — I’m just a guy who likes backpacking. It’s crazy how big it’s gotten, how much it’s grown. As a [brand] owner, you’re still a little insecure. You see someone in your shirt and think, I hope they like it.

On the CDT in 2021, it was just making hiking shirts for me and my friends. And then people were really liking it, saying how this shirt dries so much faster, etc. So we did a preorder sale and I didn’t think much of it.

Whatever that preorder sale did, I wanted to triple it. Customers purchased the 250 preorders in the first 2 weeks, so I went to the manufacturers and said let’s triple that: 750 shirts. And then we sold out. That allowed us to think a lot bigger — let’s do 3,000 shirts next year. And so we did that. And we’re still selling shirts.

But it’s really the customer feedback and excitement that carried us. Without the thru-hiking community, the thru-hikers out there loving the shirt and spreading it around, we wouldn’t have a business. Without the people in our shirts who bought the product, we wouldn’t have a company. So I just want to say thank you.

(This interview has been edited for readability and clarity.)

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