Wearing a great pair of loafers with everything from cropped, wide-leg chinos to classic suit pants to sweatpants may feel like one of the fresher flexes permeating menswear right now, but for Chris Echevarria, it’s a move that stretches back to childhood. “I was raised by my great-grandmother and my mom, and one of the things that I was required to do was go to church every weekend,” the designer of Brooklyn-based brand Blackstock & Weber explains. “The uniform for church was a pair of khakis, white shirt, penny loafers. And the loafers—and everything in that outfit—have never left my wardrobe. So I’ve always been wearing these loafers in very interesting ways.” Esquire