John Frazier dropped out of college and spends most days in the basement of his parents' Lake Bluff, Illinois, house. But his is no cautionary tale, and he's not wandering around in sweatpants. The exuberant, lanky 22-year-old is the founder and CEO of John Byron, an up-and-coming custom shirt label that is looking to bring bespoke luxury button-ups to the masses. His products don't reflect his youth. John Byron shirts are made of rich, thick fabrics cut by experienced tailors and designed to make an impression.

"So far we've got a small group of customers, but they make big purchases, which bodes well," says Frazier. "It's a sophisticated crowd, because there's something rakish about the shirts."

Frazier is banking on flexibility to expand his audience. Taking into account all the choices available to a customer building a shirt on his site – palazzi cuffs, club collars, shoulder pleats – he offers around 4 billion options. That said, he's most comfortable with the classics, and he hopes to guide customers away from mistakes. Customers can try to order a collarless tartan shirt, but they won't succeed because Frazier doesn't want to be party to their disappointment. There is, as he is eager to point out, "nothing worse than an unpleasant surprise."

But John Byron shirts do have surprises up on the sleeves. Monogrammed cuffs are an exciting possibility for anyone looking to make a statement. And statements come with each shirt: Quotes from the likes of Molière ("I prefer an interesting vice to a virtue that bores") and Mark Twain ("Go to Heaven for the climate, Hell for the company") are sewn in instead of labels. For Frazier, this level of customization runs hand in hand with a sort of rugged individualism he admires.

"I was inspired by my granddad, who was always a well-dressed guy," says Frazier. "He'd disappear into the forest for months to paint and come back with a big beard. One time he lost an eye, but he always went back in a nice shirt."

Business is young Frazier's wilderness and one gets the sense that he's unlikely to ever come back. He's enjoying watching his company grow and trying new things. He says he doesn't mind making mistakes, "so long as they are new mistakes." And he seems to mean it. For now, what separates his company from the competition is a lower price point – shirts are priced from $165 – but Frazier hopes the quality of his Italian denim, lightweight linen, and heavy oxford cloth as well as the fit will make a more lasting impression than the savings.

He carries a tape measure in his pocket and he's getting good with it. Frazier doesn't want to stay in the basement forever and he won't. [From $165; johnbyron.com]