Here’s what a new generation of dedicated craftspeople—from Tony Shirtmakers’ Tony Parrotti to Tildenshop’s Tilden Yamamoto—have learned from operating brands entirely on their own.

This versatile vest can be layered over workout gear, worn as loungewear, or paired with jeans for a cozy touch. It’s made with snuggly, double-sized fleece that has a soft feel and high pile, adding ...