CityLab has a great story about how it took about 100 drawings before Herbert Matter came up with his famous design for New Haven Railroad:
The Swiss-born photographer, designer, and Yale professor came up with New Haven Railroad’s iconic “NH” logo in 1955 after trying out dozens of other ideas.
After losing money on its freight and rail service for years, New Haven Railroad appointed the controversial Patrick B. McGinnis as its new president in 1954. As retold by Jessica Helfand for Design Observer, McGinnis’s wife, Lucille, convinced him to pursue new branding to help restore shareholders’ and passengers’ faith in the rail company.
In a period where passenger rail service in America was often seen as antiquated compared to highways and air travel, Matter’s visual identity for New Haven Railroad still appeared as fresh as anything by GM or TWA.
Matter’s stacked ”NH” logo was finalized in a red and black scheme and unveiled one year into McGinnis’s reign. Soon after, it appeared on new locomotives, lighters, pocket watches, and playing cards.