Chavarria updates familiar Dickies styles with new shapes (see: the batwing-shaped windbreaker), often playing with scale (as seen in a boxy work shirt with oversized front pockets and sleeves).

Whether it’s a chore coat or a cropped style like the classic Dickies Eisenhower jacket, a work jacket is a time-tested silhouette that’s essentially a cheat code for looking more rugged and ...