Always Free Domestic Shipping over $99

Our Story


 

 

 

At Sleepless Jack Apparel Co., custom bike geeks, college sports nuts, coffee enthusiasts, cigar aficionados, and lovers of the smell of printing press ink and green soap all come together to rock their hearts on their sleeves.

All are welcome.

Ben Runco, (the Sleepless Jack namesake) is a Southern California native and design fanboy with a love/hate realtionship with coffee shops. Immersed in the culture of iconic surf and moto brands like Quiksilver, Deus Ex Machina, and Vans, Ben brings an unpolished, hand-hewn aesthetic to his design work. Every detail of his work reflects a passion for the heratige of simple, vintage design and the laid-back vibes of SoCal living.

Will Ruggles is our print-making wizard with Americana running his veins. Born and bred in Lawrenceburg, Kentucky, he's not just living, but embracing the Bluegrass lifestyle. Standing tall and bearded like Thor's long-lost brother, he might seem a bit wild-eyed initially. But trust me, after a couple of beers and a cigar, you'll be fast friends. Will's the ink-pulling maestro, and the quality of everything we make is all thanks to his skilled hands and love for the craft.

Sleepless Jack Apparel Co. shakes up the market with tees, sweatshirts, hats, and accessories that reflect the lifestyle. Founded by Will and Ben, it's not just about making a mark—it's about building a community of rad folks. We’re all about finding common ground in the Commonwealth and beyond.