An ad for Hobo Headwear’s ‘Dennis Cap,’ created by resident graphic designer Thomas Minor.

Born and bred in the Rocky Mountains, up-and-coming brand Hobo Headwear (née Hobo Shred Wear) has slowly but surely ingrained itself into the snowboarding community. A far cry from a copy-cat company, Hobo makes original products a top priority. Owners Colin Walters, Dylan Alito and Riley Doyle design, dye, and sew their hats themselves, ensuring quality over quantity, and offering consistently unique gear.

The brand has been bringing on core riders since its inception in 2004, getting gear  on snowboarders whose passion for the mountains matches its own. Boasting a roster that’s busting at the seams with talent and style, Hobo has taken on-snow stoke and placed it in the hands of retailers across the country. Already making its mark in over 20 shops from East to West, Hobo is making big moves-- and we don’t expect things to start slowing down anytime soon.

TransWorld Business had the chance to hang out with brand mastermind Colin Walters to get a look at the who, what, where, and what’s-next for Hobo Headwear. Take note, ladies and gents, we’ve got a good feeling about this one.

Follow the jump to check out all things Hobo

Tell me a bit about how Hobo Headwear got started

We got started back in 2004 as a joke.  My best friends Tayler Doyle and Jakob Burlison were your average high school kids that were obsessed with snowboarding.  One day in the summer of 2004 Jakob came up with the idea for a company called Hobo Headwear.  By the time sophomore year started Tayler had gathered 100 bones from each Jakob and I and had three-dozen snapbacks made with big logos on the front saying “Hobo Head Wear” in all caps.  From that point on we treated it as our own little dream business and just started making whatever we wanted.  Jakob lived a town closer to the mountains and went to Evergreen High School with Dylan Alito. Jakob talked to him about wearing the hats and he’s been a part ever since.  We ran it together until high school was over and everyone went their separate ways. I decided to keep making Hobo stuff and we have been growing slowly ever since.  Alito became involved two summers ago and is one of my two partners.  Riley Doyle is the other and is Art Director as well.

What is the inspiration behind the brand?

First off, the people we make these hats for.  I’m a creator at heart and I’m passionate about fabricating original unique hats. This business helps us do exactly what we love, snowboard.  I’d say a lot of inspiration comes from that.

How have you built hype?

When we said hand-made, we meant it.

In short, we’ve been careful on the select people we put these hats on and which shops they sell out of.  Filling the Internet with Hobo Webisodes has helped too.

Another important ingredient has been the development of these hats in the past few years.  I’ve spent countless hours on creating these hats and I’ve learned some cool shit.  They are starting to come out so hot and almost every one is different.  We are so far away from the average company that orders a thousand of the same hat in the same color way.  I still don’t think I’ve ever produced more then two-dozen of the same hat and everyone at this point still runs through my hands before landing on your head.

What's the story behind the name?

Back in ’04 the cool thing going on was wearing tall beanies with a bunch of “sag” on them.  To Jakob this looked like the way bums wore their beanies, so from that he came up with Hobo Head Wear.  The name changed to Hobo Shred Wear in 2008 when I registered the company, but funny enough we will be returning to our original name shortly.

Who all is part of the Hobo crew?

We truly are special because we are made up of so many awesome individuals.The company is owned by Dylan Alito, Riley Doyle, and I. Dylan has been helping out a lot with the marketing and financially really supporting us, and Riley has earned his title as the Art Director after this summer. It’s amazing to be working with such a high caliber of human beings.  It makes me work harder and longer and have high expectations for the other people involved.  And that's where our snowboard team comes in:

Dylan Alito, Billy Mackey, Chris Sypert, Josh Bishop, and Kyle Hay; all these dudes were part of Hobo around or before 2007. Over the past five seasons, plus a few summers at Windells, the current team is stacked by: Blake Rhodes Reid, Jared Jordan, Michael Wick, Red Gerard --dude freaked me out!  He was so small and just chuckin’ meat off Park Lanes jumps.  I think he was seven at the time--first sponsor, I’m claiming it Justin Fronius, Austin Julik-Heine, Johnny Lazzareschi, Derrek Lever, Blake Gies, Brandon Hobush, Aidan Flanagan, Boody, Danimals, Mark Wilson, Jasper Kahn, Dylan Dragotta, Stevie Meskill, Squiggs, Riley Nickerson, Jordan Smalls, Mary Rand, Mike Cassanova, and Jaeger Bailey. Whew!

I couldn’t be happier having them apart of this and I feel that way across the board.

What other aspects of the industry is Hobo involved in?

Hobo hats, created specially for the premiere of Keep The Change’s movie, ‘Holy Smokes’

We also support three film production companies:  Jake Durham with Make, John Stark with Working for the City, and Rob Balding with Keep the Change.  I am very excited about producing hats for these companies this fall.

Brand philosophy in one word:


Do you make the hats yourself?

Yes, I order the hats blank wholesale and then add custom touches to them like acid washing or pattern printing and I take care of sewing all the patches myself.  I’m actually in the process of handing that job off to Billy Mackey and another friend with some sewing skills.  The leather patches are all produced by Riley Doyle and he truly is a magician at producing those things.

How many options/designs do you currently offer?

This winter’s line we are offering eight styles of hats each with multiple color options--26 different hats to be exact.  We also are offering a Casual Jacket and 2 styles of shades in select shops.

Do you have any other Hobo Shred Wear gear?

We have messed around with various products including tees, hoodies, jackets, sunglasses, and face masks, but hats are our forte.  We also have a been working on making mittens the past two years. Pretty excited about those things but we they will come out when they are ready.

Hobo team rider Derrek Lever shows off a fine pair of Hobo gloves

Are your hats in any shops so far?

Indeed, we have taken this process on slowly and like to work with legit skate/snow shops.  As of this October we are in twenty-plus locations, including: Damage, Cal Surf, Recess, Stevens Pass, and Cuckoos Nest. In Colorado, Hobo has hats at BC (Park Meadows and Boulder), Satellite, Thrifty Stick, 720 Board Shop, Woodward at Copper, and Big Hit. Over on the East Coast, we are currently distributing to Ice Coast, Reciprocal and 2nd Nature in New York; Utopia, Capsule, and Rampage in Connecticut; Lahouts, plus Eastern Boarder in New Hampshire.

We will also be offering limited runs of hats online starting in January 2013.

What are some of the dream doors you'd like to get the brand into?

Dream shops would include any that support the same people we do, like Active, because they help out Johnny and Jordan.  Shops like The Youth Shelter Supply too because they are putting a lot into the snowboard industry.  The owner of that shop makes the hottest Mid-West shop video year after year.  Those are the type of shops we want to be in.

What is your goal with Hobo hats?

Running a business that allows my friends and I to live a life where we all are doing what we love.  Living a life that is driven by personal motivation everyday because I seriously love what I do.

The cap snatcher; one of the many ingenious details that make Hobo a stand-out

We’ve been in the game for some time but I do think things will continue to move faster and faster.  I hope, like any good company, we can take the industry by storm and earn money that will support all the people that helped push it.

I want to take advantage of the ridiculously talented, unique, and young team I have in front of me right now…maybe spend a couple years filming a documentary style snowboard video.  Yeah, I’d like to that in the next 5 years...Also, shifting this company even more into our rider’s hands.