Chris Tag works as an art director for an ad agency. He knows what’s ugly. He knows what’s boring. Man bags, he says, have been both—up until now. Using an industrial Tacsew machine and recycled vinyl from highway billboards, Tag, 38, has been crafting shoulder sacks with hell-raising emblems such as motorcycles and skulls out of his Evanston home.

“They defy conventional wisdom,” says the designer, who calls his enterprise Defy Bags. Made of 90 percent recycled material and stair tread from Home Depot, the bags (from $135) have caught on simply by word of mouth. Next up: a women’s line. defybags.com

Photography: Tyllie Barbosa