David D. Doniger cut his teeth in the mercurial, idiosyncratic world of hat-making, and after relocating to New York, began importing checked caps and sporting headwear that drew on what he remembered from his time in Scotland. Branding them under the name McGregor, he quickly found that, in a city of small but fiercely competitive apparel players, the right combination of foreignness and practicality could translate into real traction.

By the early ’30s, while American sportswear was still coalescing as a category, McGregor had already started performing a kind of cultural arithmetic — taking the existing lexicon of menswear and expanding it into coordinated sets. This approach, which might otherwise read as pragmatic, actually gestured toward a radical recalibration: lightweight shirts and separates were at once functional and semiotic, announcing, through their very existence, a shift in how men wanted to inhabit their bodies socially — on campuses, on tennis courts, at golf clubs, in the sweep of city life. McGregor also understood influence, and by deliberately associating itself with universities, athletes, and nascent style hubs, it positioned itself at the leading edge of what would eventually be recognized as American casualwear.

Through the ’40s and into the postwar period, that instinct only deepened: knits and shirting gave way to purposeful outerwear — leather jackets, sports coats, garments developed with actual use in mind—all while retaining a certain unassuming elegance. Then, in the mid-to-late ’40s, came the Drizzler: short, water-resistant, light, and versatile—simultaneously casual enough for the course and sufficiently polished for everyday life—a jacket that didn’t just fill a slot in the wardrobe but effectively created a new category where function and form were no longer separable.