Hailing from Sudbury, Mass, Category Five founder Jason Shuman has a familial lineage rooted in shoe folk.

His grandfather opened and operated a shoe component manufacturing company in Brockton 30 years ago. After buying a standard pair of boat shoes in college, Shuman came to the realization that things in the leathery foot sheath world had gotten stale for fellas over the years. In his eyes, the solution lay with the Millennials.

“When it comes to a startup [raising capital], investors want outside thinking, and fresh new outlooks to bring passion back to where it has been lost over time,” says Shuman.

After amassing advisers and investors from some of the brains behind Clark’s, Sperry Top Sider, and Puma, Shuman got Category Five off the ground a couple years back in order to counter stale brands that had been around for a long time in the old stodgy loafer space. Touting what he calls the “Millennial mindset (“chasing after a dream and walking confidently while following life’s passions,” according to him), the goal was to create sharp-looking customizable comfortable leather footwear with a lower price point.

Shuman says since Category Five sells direct to the consumer via the website, and hand pre-treats all shoes with the same protectant you’d normally have to buy separately (“ours makes beer bead up to be wiped right off, like Gore-Tex,” he says), the company can maintain lower costs for a higher quality loafer using soft-tumbled leathers, and a zero-friction Achilles heel wrap, along with the same kind of foot beds used in athletic running shoes, making all-day hoofing around the city tolerable and stylish.

Depending on your overall thoughts on boat shoes, that is.

CATEGORY FIVE. $80-125. NOW AVAILABLE ONLINE.